Product Name

  • Name

    N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

  • EINECS
  • CAS No. 477600-74-1
  • Article Data38
  • CAS DataBase
  • Density 1.198 g/cm3
  • Solubility
  • Melting Point
  • Formula C13H19N5
  • Boiling Point
  • Molecular Weight 245.327
  • Flash Point
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 477600-74-1 (N-methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine)
  • Hazard Symbols
  • Synonyms 1H-Pyrrolo[2,3-d]pyrimidin-4-amine,N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]- (9CI);(3R,4R)-Methyl{(4-methylpiperidin-3-yl)(7H-pyrrolo[2,3-d]pyrimidin-4-yl)}amine;
  • PSA 56.84000
  • LogP 1.72090

Synthetic route

(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine

(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-2-chloro-N-methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With hydrogenchloride; palladium 10% on activated carbon; hydrogen In water at 65 - 75℃; under 1551.49 Torr; for 3h; Inert atmosphere;96%
With triethylsilane; 5%-palladium/activated carbon; acetic acid In methanol at 30℃; for 0.166667h;93.1%
With 10 wt% Pd(OH)2 on carbon; hydrazine hydrate; acetic acid In ethanol at 70 - 75℃; for 2h; Reagent/catalyst;75.8%
(3R,4R)-tert-butyl 4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
1450663-24-7

(3R,4R)-tert-butyl 4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With zinc dibromide In dichloromethane for 12h;95%
((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amine

((3R,4R)-1-benzyl-4-methylpiperidin-3-yl)-N-methyl-(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal; hydrogen In methanol at 45℃; under 6000.6 Torr;93%
With 20% palladium hydroxide-activated charcoal; ammonium formate In methanol at 60℃; for 6h; Solvent; Reagent/catalyst; Temperature; Inert atmosphere;93.3%
With 20% palladium hydroxide-activated charcoal; hydrogen; acetic acid In methanol; water at 50℃; under 3000.3 - 4500.45 Torr; for 12h;92.38%
C20H25N5*CH2O2

C20H25N5*CH2O2

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane; water at 20℃; for 1h;91%
C27H31N5

C27H31N5

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In ethanol at 60 - 70℃;85%
3-(3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-(yl)amino)piperidin-1-yl)-3-oxopropionic acid

3-(3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-(yl)amino)piperidin-1-yl)-3-oxopropionic acid

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With sulfuric acid at 90℃;28.9%
(S)-5-hydroxypiperidin-2-one
24211-54-9

(S)-5-hydroxypiperidin-2-one

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1.1: 1H-imidazole / 24.5 h / 5 - 20 °C
2.1: 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
2.2: 2 h
3.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C
3.2: 2 h / -78 °C
4.1: magnesium / diethyl ether
4.2: 0.25 h / -20 °C
4.3: 2 h / 20 °C
5.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
7.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
8.1: zinc dibromide / dichloromethane / 12 h
View Scheme
(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one
176966-76-0

(5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: 1,4-diaza-bicyclo[2.2.2]octane; n-butyllithium / tetrahydrofuran / 1 h / -78 °C
1.2: 2 h
2.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C
2.2: 2 h / -78 °C
3.1: magnesium / diethyl ether
3.2: 0.25 h / -20 °C
3.3: 2 h / 20 °C
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
5.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
6.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
7.1: zinc dibromide / dichloromethane / 12 h
View Scheme
7-deazaadenine
1500-85-2

7-deazaadenine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: water; acetonitrile / 0.25 h / 20 °C
1.2: 1 h
2.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
3.1: zinc dibromide / dichloromethane / 12 h
View Scheme
tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate
176966-77-1

tert-butyl (5S)-5-tert-butyldiphenylsilyloxy-piperidine-2-one-1-carboxylate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: n-butyllithium; hexamethyldisilazan / tetrahydrofuran; hexane / 0.5 h / -78 °C
1.2: 2 h / -78 °C
2.1: magnesium / diethyl ether
2.2: 0.25 h / -20 °C
2.3: 2 h / 20 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
5.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
6.1: zinc dibromide / dichloromethane / 12 h
View Scheme
tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate
176966-78-2

tert-butyl (5S)-5-(tert-butyldiphenylsilyloxy)-3,4-dehydro-piperidine-2-one-1-carboxylate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: magnesium / diethyl ether
1.2: 0.25 h / -20 °C
1.3: 2 h / 20 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
3.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
4.1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
5.1: zinc dibromide / dichloromethane / 12 h
View Scheme
(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester
176966-79-3

(4R,5S)-5-(tert-Butyl-diphenyl-silanyloxy)-4-methyl-2-oxo-piperidine-1-carboxylic acid tert-butyl ester

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere
2: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
3: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
4: zinc dibromide / dichloromethane / 12 h
View Scheme
tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate
176966-86-2

tert-butyl (3S,4R)-3-(tert-butyldiphenylsilyloxy)-4-methyl-piperidine-1-carboxylate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: tetrabutyl ammonium fluoride / tetrahydrofuran / 2 h / 20 °C
2: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
3: zinc dibromide / dichloromethane / 12 h
View Scheme
tert-butyl (3S,4R)-3-hydroxy-4-methyl-piperidine-1-carboxylate
176966-87-3

tert-butyl (3S,4R)-3-hydroxy-4-methyl-piperidine-1-carboxylate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: di-isopropyl azodicarboxylate; triphenylphosphine / 1,4-dioxane / 2 h / 100 °C
2: zinc dibromide / dichloromethane / 12 h
View Scheme
Multi-step reaction with 3 steps
1.1: triphenylphosphine; di-isopropyl azodicarboxylate / 1,4-dioxane / 4 h / 0 - 90 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 0.5 h / 20 °C
2.2: 24 h / 20 °C
3.1: hydrogenchloride / tetrahydrofuran / 1 h / 20 °C
View Scheme
methyl-(1-trityl-4-methylpiperidin-3-yl)carbamate
1616760-91-8

methyl-(1-trityl-4-methylpiperidin-3-yl)carbamate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
2.1: ethyl acetate / 3 h / 25 - 30 °C
3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
5.2: Reflux
View Scheme
Multi-step reaction with 6 steps
1.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
2.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
3.1: water; methanol / 8 - 9 h / 20 - 70 °C
4.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
5.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
6.2: Reflux
View Scheme
Multi-step reaction with 7 steps
1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
2: ethyl acetate / 3 h / 25 - 30 °C
3: potassium carbonate / ethyl acetate; water / pH 9 - 10
4: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
5: sodium hydroxide / water; acetone / 55 - 60 °C
6: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
7: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
1-triryI-N,4-dimethylpiperidin-3-amine hydrochloride

1-triryI-N,4-dimethylpiperidin-3-amine hydrochloride

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: water; methanol / 8 - 9 h / 20 - 70 °C
2.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
3.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
4.2: Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: potassium carbonate / water / pH 7 - 8
2.1: ethyl acetate / 3 h / 25 - 30 °C
3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
5.2: Reflux
View Scheme
Multi-step reaction with 6 steps
1: water; methanol / 8 - 9 h / 20 - 70 °C
2: potassium carbonate / ethyl acetate; water / pH 9 - 10
3: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
4: sodium hydroxide / water; acetone / 55 - 60 °C
5: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
6: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
1-triryI-N,4-dimethylpiperidin-3-amine
1616833-40-9

1-triryI-N,4-dimethylpiperidin-3-amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: ethyl acetate / 3 h / 25 - 30 °C
2.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
3.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
4.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
4.2: Reflux
View Scheme
Multi-step reaction with 5 steps
1.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
2.1: water; methanol / 8 - 9 h / 20 - 70 °C
3.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
4.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
5.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
5.2: Reflux
View Scheme
Multi-step reaction with 6 steps
1: ethyl acetate / 3 h / 25 - 30 °C
2: potassium carbonate / ethyl acetate; water / pH 9 - 10
3: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
4: sodium hydroxide / water; acetone / 55 - 60 °C
5: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
6: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
(3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine di-p-toluyl-D-tartaric acid salt

(3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine di-p-toluyl-D-tartaric acid salt

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
2.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
3.2: Reflux
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / ethyl acetate; water / pH 9 - 10
2: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
3: sodium hydroxide / water; acetone / 55 - 60 °C
4: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 5 steps
1: potassium carbonate / ethyl acetate; water / pH 9 - 10
2: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
3: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C
4: sodium hydroxide / water; acetone / 50 - 55 °C
5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
(3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine
1616760-93-0

(3R,4R)-1-trityl-N,4-dimethylpiperidin-3-amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
2.2: Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
2: sodium hydroxide / water; acetone / 55 - 60 °C
3: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
2: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C
3: sodium hydroxide / water; acetone / 50 - 55 °C
4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
2,4-dichloro-7-p-methylbenzenesulfonyl-7H-pyrrole[2,3-d]pyrimidin-4-amine
934524-10-4

2,4-dichloro-7-p-methylbenzenesulfonyl-7H-pyrrole[2,3-d]pyrimidin-4-amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
2.2: Reflux
View Scheme
Multi-step reaction with 2 steps
1.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
2.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
2.2: Reflux
View Scheme
Multi-step reaction with 4 steps
1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C
2: sodium hydroxide / water; acetone / 55 - 60 °C
3: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
4: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine
90213-66-4

2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C
2.1: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
3.2: Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C
2.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
3.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
3.2: Reflux
View Scheme
Multi-step reaction with 5 steps
1: sodium hydroxide / water; acetone / 2 - 3 h / 0 - 30 °C
2: potassium carbonate / N,N-dimethyl-formamide / 10 h / 70 - 75 °C
3: sodium hydroxide / water; acetone / 55 - 60 °C
4: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
5: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
C39H38ClN5O2S
1616760-94-1

C39H38ClN5O2S

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: C39H38ClN5O2S With palladium 10% on activated carbon; hydrogen In methanol at 45 - 55℃; under 3750.38 Torr; for 10h;
Stage #2: With sodium hydroxide In methanol; water Reflux;
Multi-step reaction with 3 steps
1: sodium hydroxide / water; acetone / 55 - 60 °C
2: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 3 steps
1: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C
2: sodium hydroxide / water; acetone / 50 - 55 °C
3: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
C20H24ClN5O2S
1616760-95-2

C20H24ClN5O2S

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / water; acetone / 50 - 55 °C
2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
C32H32ClN5
1616760-96-3

C32H32ClN5

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
2: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine
1616760-97-4

N-((3R,4R)-4-methyl-piperidin-3-yl)-N-methyl-2-chloro-7H-pyrrolo[2,3-D]pyrimidine-4-amine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
With 10% palladium hydroxide on charcoal; hydrogen In methanol at 50 - 55℃; under 5250.53 - 6000.6 Torr; for 4h; Solvent; Reagent/catalyst; Temperature; Pressure; Time;25 g
O-methyl-N-(4-methylpyridin-3-yl)carbamate
694495-63-1

O-methyl-N-(4-methylpyridin-3-yl)carbamate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
2: triethylamine / acetonitrile / 10 h / 65 - 70 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
4: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
5: water; methanol / 8 - 9 h / 20 - 70 °C
6: potassium carbonate / ethyl acetate; water / pH 9 - 10
7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
8: sodium hydroxide / water; acetone / 55 - 60 °C
9: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 10 steps
1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
2: triethylamine / acetonitrile / 10 h / 65 - 70 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
4: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
5: water; methanol / 8 - 9 h / 20 - 70 °C
6: potassium carbonate / ethyl acetate; water / pH 9 - 10
7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
8: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C
9: sodium hydroxide / water; acetone / 50 - 55 °C
10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 7 steps
1.1: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
2.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
4.1: ethyl acetate / 3 h / 25 - 30 °C
5.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
6.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
7.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
7.2: Reflux
View Scheme
3-amino-4-methylpyridine
3430-27-1

3-amino-4-methylpyridine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: potassium tert-butylate / 1 h / 10 - 15 °C
2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
3: triethylamine / acetonitrile / 10 h / 65 - 70 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
5: ethyl acetate / 3 h / 25 - 30 °C
6: potassium carbonate / ethyl acetate; water / pH 9 - 10
7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
8: sodium hydroxide / water; acetone / 55 - 60 °C
9: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 10 steps
1: potassium tert-butylate / 1 h / 10 - 15 °C
2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
3: triethylamine / acetonitrile / 10 h / 65 - 70 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
5: ethyl acetate / 3 h / 25 - 30 °C
6: potassium carbonate / ethyl acetate; water / pH 9 - 10
7: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
8: trifluoroacetic acid / dichloromethane / 3 h / 5 - 10 °C
9: sodium hydroxide / water; acetone / 50 - 55 °C
10: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
Multi-step reaction with 11 steps
1: potassium tert-butylate / 1 h / 10 - 15 °C
2: 5wt.% Rh on activated alumina; hydrogen / acetic acid / 10 h / 70 - 75 °C / 5250.53 - 6000.6 Torr
3: triethylamine / acetonitrile / 10 h / 65 - 70 °C
4: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
5: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
6: water; methanol / 8 - 9 h / 20 - 70 °C
7: potassium carbonate / ethyl acetate; water / pH 9 - 10
8: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
9: sodium hydroxide / water; acetone / 55 - 60 °C
10: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
11: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
methyl-(4-methylpiperidin-3-yI)carbamate

methyl-(4-methylpiperidin-3-yI)carbamate

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
3.1: ethyl acetate / 3 h / 25 - 30 °C
4.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
5.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
6.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
6.2: Reflux
View Scheme
Multi-step reaction with 7 steps
1.1: triethylamine / acetonitrile / 10 h / 65 - 70 °C
2.1: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
3.1: hydrogenchloride / ethyl acetate / 0.5 h / 25 - 30 °C / pH 2 - 3
4.1: water; methanol / 8 - 9 h / 20 - 70 °C
5.1: potassium carbonate / ethyl acetate; water / pH 9 - 10
6.1: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
7.1: palladium 10% on activated carbon; hydrogen / methanol / 10 h / 45 - 55 °C / 3750.38 Torr
7.2: Reflux
View Scheme
Multi-step reaction with 8 steps
1: triethylamine / acetonitrile / 10 h / 65 - 70 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 4 h / 60 - 70 °C / Inert atmosphere
3: ethyl acetate / 3 h / 25 - 30 °C
4: potassium carbonate / ethyl acetate; water / pH 9 - 10
5: potassium carbonate / acetonitrile; N,N-dimethyl-formamide / 6 h / 70 - 75 °C
6: sodium hydroxide / water; acetone / 55 - 60 °C
7: trifluoroacetic acid / dichloromethane / 1 h / 5 - 10 °C
8: 10% palladium hydroxide on charcoal; hydrogen / methanol / 4 h / 50 - 55 °C / 5250.53 - 6000.6 Torr
View Scheme
N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine
477600-70-7

N-(3R,4R)-(1-benzyl-4-methylpiperidin-3-yl)-methylamine

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium carbonate / water / 48 h / 110 °C / Sealed tube
2: hydrogen; palladium 10% on activated carbon; 20% palladium hydroxide-activated charcoal / methanol / 45 °C / 6000.6 Torr
View Scheme
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

formaldehyd
50-00-0

formaldehyd

C14H21N5

C14H21N5

Conditions
ConditionsYield
With acetic acid; zinc In water at 20℃; Reagent/catalyst; Concentration;99.25%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

citric acid
77-92-9

citric acid

Tofacitinib citrate

Tofacitinib citrate

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 80℃; for 0.166667h;96.4%
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 40℃; for 20h; Inert atmosphere;
Stage #2: citric acid In water; butan-1-ol at 22 - 81℃; for 2.5h; Inert atmosphere;		93%
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 35 - 45℃; for 7h; Inert atmosphere;
Stage #2: citric acid In water; butan-1-ol at 20 - 90℃; Inert atmosphere;		90.3%
...Expand
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

cyanoacetic acid
372-09-8

cyanoacetic acid

tasocitinib

tasocitinib

Conditions
ConditionsYield
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; Schlenk technique;96%
With potassium carbonate; 4-pyrrolidin-1-ylpyridine; diisopropyl-carbodiimide In dichloromethane at 35℃; for 1h; pH=7 - 8; Solvent; Reagent/catalyst; Temperature; Inert atmosphere; Industrial scale;89.7%
With 1,1'-carbonyldiimidazole In dichloromethane at 40℃; for 10h;89.21%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

tasocitinib

tasocitinib

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In methanol at 5 - 20℃; for 8h; Temperature; Solvent;91%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 20 - 30℃; for 24h;78%
With 1,8-diazabicyclo[5.4.0]undec-7-ene In tetrahydrofuran at 60 - 65℃; Solvent;76.9%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

cycl-isopropylidene malonate
2033-24-1

cycl-isopropylidene malonate

3-(3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-(yl)amino)piperidin-1-yl)-3-oxopropionic acid

3-(3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-(yl)amino)piperidin-1-yl)-3-oxopropionic acid

Conditions
ConditionsYield
In acetonitrile at 20℃; Solvent; Temperature;87.7%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

ethyl 2-cyanoacetate
105-56-6

ethyl 2-cyanoacetate

3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile citrate

3-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)-3-oxopropanenitrile citrate

Conditions
ConditionsYield
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; ethyl 2-cyanoacetate With 1,8-diazabicyclo[5.4.0]undec-7-ene In butan-1-ol at 40℃; for 18h;
Stage #2: With citric acid monohydrate In water; butan-1-ol at 80℃; for 0.5h;		87.6%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

succinimidyl cyanoacetate
56657-76-2

succinimidyl cyanoacetate

tasocitinib

tasocitinib

Conditions
ConditionsYield
In ethanol at 20℃; for 2h;86%
In ethanol at 25℃; for 3h; Temperature; Time;
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In toluene at 40℃; for 2h; Large scale;
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

diethyl malonate
105-53-3

diethyl malonate

C18H25N5O3

C18H25N5O3

Conditions
ConditionsYield
With triethylamine In methanol for 9h; Reflux;85%
5-methyl-1,2-oxazole-4-carboxylic acid
42831-50-5

5-methyl-1,2-oxazole-4-carboxylic acid

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)(5-methylisoxazol-4-yl)methanone

((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)(5-methylisoxazol-4-yl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice; Enzymatic reaction;80%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

cyanoacetic acid
372-09-8

cyanoacetic acid

N-methyl-N-[(3R,4R)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine cyanoacetate

N-methyl-N-[(3R,4R)-4-methyl-3-piperidyl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine cyanoacetate

Conditions
ConditionsYield
In acetonitrile at 60 - 65℃;80%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

cyanoacetic acid
372-09-8

cyanoacetic acid

citric acid
77-92-9

citric acid

Tofacitinib citrate

Tofacitinib citrate

Conditions
ConditionsYield
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; cyanoacetic acid With benzotriazol-1-ol In dichloromethane at 20℃; for 12h;
Stage #2: citric acid In acetone at 40℃; for 2h;		70%
Stage #1: cyanoacetic acid With pivaloyl chloride; triethylamine In dichloromethane at -15 - 0℃; for 2.5h;
Stage #2: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate In dichloromethane at 0℃; for 1h;
Stage #3: citric acid In water; acetone at 55 - 65℃;		67.3%
...Expand
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

1-cyano-cyclopropanecarboxylic acid
6914-79-0

1-cyano-cyclopropanecarboxylic acid

1-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carbonyl)cyclopropanecarbonitrile

1-((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carbonyl)cyclopropanecarbonitrile

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at -10 - 10℃;56.82%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

5-cyclopropylisoxazole-4-carboxylic acid
124845-04-1

5-cyclopropylisoxazole-4-carboxylic acid

(5-cyclopropylisoxazol-4-yl)((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)piperidin-1-yl)methanone

(5-cyclopropylisoxazol-4-yl)((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidine-4-yl)amino)piperidin-1-yl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice;53%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

5-Isopropyl-4-isoxazolecarboxylic acid
134541-05-2

5-Isopropyl-4-isoxazolecarboxylic acid

C20H26N6O2

C20H26N6O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice;53%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

N-((tert-butyloxy)carbonyl)iminodiacetic acid
56074-20-5

N-((tert-butyloxy)carbonyl)iminodiacetic acid

C30H41N11O2

C30H41N11O2

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide at 5 - 30℃; Reagent/catalyst; Temperature;43.7%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

2,2'-(4-methoxybenzyl)imino-diacetic acid
1217900-36-1

2,2'-(4-methoxybenzyl)imino-diacetic acid

C30H41N11O2

C30H41N11O2

Conditions
ConditionsYield
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; N-4-methoxyphenylmethyliminodiacetic acid With dmap; dicyclohexyl-carbodiimide at 10 - 35℃;
Stage #2: With palladium on activated charcoal; hydrogen at -10℃; under 11251.1 Torr;		40.8%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

methoxycarbonylimino-di-acetic acid

methoxycarbonylimino-di-acetic acid

C30H41N11O2

C30H41N11O2

Conditions
ConditionsYield
With 4-pyrrolidin-1-ylpyridine; dicyclohexyl-carbodiimide at 5 - 40℃; Temperature;35%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

methyl chloroformate
79-22-1

methyl chloroformate

methyl (3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidine-1-carboxylate

methyl (3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidine-1-carboxylate

Conditions
ConditionsYield
With potassium carbonate In dichloromethane at 0 - 20℃; for 0.333333h; Inert atmosphere; Schlenk technique;34%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

(S)-4-nitrophenyl 3-hydroxypyrrolidine-1-carboxylate
1269920-81-1

(S)-4-nitrophenyl 3-hydroxypyrrolidine-1-carboxylate

((S)-3-hydroxypyrrolidin-1-yl)((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methanone
1259403-96-7

((S)-3-hydroxypyrrolidin-1-yl)((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)methanone

Conditions
ConditionsYield
With triethylamine In tert-butyl alcohol at 100℃; for 48h;33%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

acryloyl chloride
814-68-6

acryloyl chloride

1-((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one

1-((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)prop-2-en-1-one

Conditions
ConditionsYield
In dichloromethane at 0℃; for 1h;32%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

N-benzyliminodiacetic acid
3987-53-9

N-benzyliminodiacetic acid

C30H41N11O2

C30H41N11O2

Conditions
ConditionsYield
Stage #1: tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate; N-benzyliminodiacetic acid With dmap; dicyclohexyl-carbodiimide at 10 - 30℃;
Stage #2: With palladium on activated charcoal; hydrogen under 15001.5 Torr; for 10h; Temperature;		32%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

5-Ethyl-4-isoxazolecarboxylic acid
134541-03-0

5-Ethyl-4-isoxazolecarboxylic acid

(5-ethylisoxazol-4-yl)((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]Pyrimidin-4-yl)amino)piperidin-1-yl)methanone

(5-ethylisoxazol-4-yl)((3R,4R)-4-methyl-3-(methyl-(7H-pyrrolo[2,3-d]Pyrimidin-4-yl)amino)piperidin-1-yl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 1.5h; Inert atmosphere; Cooling with ice;31%
3-methyl isoxazole-4-carboxylic acid
17153-20-7

3-methyl isoxazole-4-carboxylic acid

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)(3-methylisoxazol-4-yl)methanone

((3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidin-1-yl)(3-methylisoxazol-4-yl)methanone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N,N-tetramethyluroniumhexafluorophosphate In dichloromethane at 20℃; for 3h; Inert atmosphere; Cooling with ice;23%
tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate
477600-74-1

tert-butyl (3R,4R)-4-methyl-3-(methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

acetyl chloride
75-36-5

acetyl chloride

1-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone

1-{(3R,4R)-4-Methyl-3-[methyl-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amino]-piperidin-1-yl}-ethanone

Conditions
ConditionsYield
In pyridine; dichloromethane at 20℃; for 18h;15%

N-Methyl-N-((3R,4R)-4-methylpiperidin-3-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine Specification

This chemical is called 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]-, and its systematic name is N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]-7H-pyrrolo[2,3-d]pyrimidin-4-amine. With the molecular formula of C13H19N5, its molecular weight is 245.32. The CAS registry number of this chemical is 477600-74-1.

Other characteristics of the 7H-Pyrrolo[2,3-d]pyrimidin-4-amine, N-methyl-N-[(3R,4R)-4-methyl-3-piperidinyl]- can be summarised as followings: (1)ACD/LogP: 1.54; (2)# of Rule of 5 Violations: 0; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 5; (8)#H bond donors: 2; (9)#Freely Rotating Bonds: 2; (10)Polar Surface Area: 56.84 Å2; (11)Index of Refraction: 1.636; (12)Molar Refractivity: 73.5 cm3; (13)Molar Volume: 204.8 cm3; (14)Polarizability: 29.13×10-24cm3; (15)Surface Tension: 56 dyne/cm; (16)Density: 1.197 g/cm3.

You can still convert the following datas into molecular structure:
1.SMILES: C[C@@H]3CCNC[C@@H]3N(C)c2ncnc1nccc12
2.InChI: InChI=1/C13H19N5/c1-9-3-5-14-7-11(9)18(2)13-10-4-6-15-12(10)16-8-17-13/h4,6,8-9,11,14H,3,5,7H2,1-2H3,(H,15,16,17)/t9-,11+/m1/s1
3.InChIKey: XRIARWQZLGCQDM-KOLCDFICBX

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