Product Name

  • Name

    4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid

  • EINECS 629-968-8
  • CAS No. 641569-94-0
  • Article Data16
  • CAS DataBase
  • Density 1.336 g/cm3
  • Solubility
  • Melting Point
  • Formula C17H14N4O2
  • Boiling Point 587.927 °C at 760 mmHg
  • Molecular Weight 306.324
  • Flash Point 309.367 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 641569-94-0 (4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid)
  • Hazard Symbols
  • Synonyms 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino] benzoic acid;4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid;Benzoic acid,4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino];4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinylJaminoJbenzoicacid;4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid;4-methyl-3-(4-(pyridine-3-yl)pyrimidin-2-ylamino)benzoic acid;3-(4-(pyridin-3-yl)pyrimidin-2-ylamino)-4-methylbenzoic acid;BEN740;
  • PSA 88.00000
  • LogP 3.36180

Synthetic route

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzonitrile

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzonitrile

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
With water; sodium hydroxide In ethanol at 100℃; for 5h;92%
4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
With sodium hydroxide In ethanol; water at 45℃; for 2h;90%
With sodium hydroxide In ethanol; water at 45 - 50℃; for 4h;87%
Stage #1: 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester With sodium hydroxide In ethanol; water at 45℃; for 2.5h;
Stage #2: With hydrogenchloride In ethanol; water for 1.5h;
Stage #1: 4-methyl-3-[[4-(3-pyridyl)-2-pyrimidinyl]amino]benzoic acid ethyl ester With sodium hydroxide In methanol; dichloromethane at 20℃;
Stage #2: With water
With ethanol; water; sodium hydroxide at 45 - 50℃;
butyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate

butyl 4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In tetrahydrofuran; methanol at 20℃; for 12h;90%
N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride
1207534-99-3

N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Stage #1: N-(2-methyl-5-nitrophenyl)guanidinium hydrochloride; 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one With potassium carbonate In propan-1-ol for 24h; Reflux;
Stage #2: With sodium hydroxide In propan-1-ol
Stage #3: With hydrogenchloride In propan-1-ol		87%
methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate
917392-54-2

methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 20℃; for 8h;60%
Stage #1: methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate With sodium hydroxide; water; butan-1-ol for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride; water; butan-1-ol
Stage #1: methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate With sodium hydroxide; water; butan-1-ol for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride; water In butan-1-ol at 20℃;
Stage #1: methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate With sodium hydroxide; water In butan-1-ol for 0.5h; Heating / reflux;
Stage #2: With hydrogenchloride In water; butan-1-ol at 20℃;
With water; potassium hydroxide at 60℃; Reagent/catalyst;5.63 g
3-guanidino-4-methylbenzoic acid methyl ester
1025716-98-6

3-guanidino-4-methylbenzoic acid methyl ester

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

A

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

B

methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate
917392-54-2

methyl 4-methyl-3 -[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoate

Conditions
ConditionsYield
Stage #1: 3-guanidino-4-methylbenzoic acid methyl ester; 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one With sodium hydroxide; ethanol for 16h; Heating / reflux;
Stage #2: With hydrogenchloride; water pH=~ 3 - 4;
...Expand
3-amino-p-toluic acid
2458-12-0

3-amino-p-toluic acid

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: sulfuric acid / 12 h / Reflux; Inert atmosphere
2: hydrogenchloride / ethanol; water / 15 h / Reflux
3: ammonium nitrate / 0.5 h / 0 °C
4: sodium hydroxide / butan-1-ol / 72 h / Reflux; Inert atmosphere
5: sodium hydroxide / ethanol; water / 4 h / 45 - 50 °C
View Scheme
3-amino-4-methylbenzoic acid ethyl ester
41191-92-8

3-amino-4-methylbenzoic acid ethyl ester

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: hydrogenchloride / ethanol; water / 15 h / Reflux
2: ammonium nitrate / 0.5 h / 0 °C
3: sodium hydroxide / butan-1-ol / 72 h / Reflux; Inert atmosphere
4: sodium hydroxide / ethanol; water / 4 h / 45 - 50 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / ethanol; water
1.2: 1.5 h / 70 °C
2.1: potassium carbonate / propan-1-ol / 24 h / Reflux
3.1: sodium hydroxide / dichloromethane; methanol / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: hydrogenchloride / toluene; ethanol; water / Reflux
1.2: 1 h / 5 - 10 °C
2.1: sodium hydroxide / iso-butanol / Reflux
3.1: sodium hydroxide; water; ethanol / 45 - 50 °C
View Scheme
3-guanidino-4-methylbenzoic acid ethyl ester nitrate
641569-96-2

3-guanidino-4-methylbenzoic acid ethyl ester nitrate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / butan-1-ol / 72 h / Reflux; Inert atmosphere
2: sodium hydroxide / ethanol; water / 4 h / 45 - 50 °C
View Scheme
C11H15N3O2
641569-95-1

C11H15N3O2

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: ammonium nitrate / 0.5 h / 0 °C
2: sodium hydroxide / butan-1-ol / 72 h / Reflux; Inert atmosphere
3: sodium hydroxide / ethanol; water / 4 h / 45 - 50 °C
View Scheme
3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate
1025716-99-7

3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Stage #1: 3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate; 3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one With sodium hydroxide In butan-1-ol for 12h; Inert atmosphere; Reflux;
Stage #2: With water; sodium hydroxide In butan-1-ol at 25 - 125℃; for 0.333333h;
Stage #3: With hydrogenchloride In water; butan-1-ol at 25 - 35℃; for 1h;		8.7 g
methyl-3-pyridylketone
350-03-8

methyl-3-pyridylketone

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 2 h / 25 - 80 °C / Inert atmosphere
2.1: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Reflux
2.2: 0.33 h / 25 - 125 °C
2.3: 1 h / 25 - 35 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium methylate / toluene / 16 h / 25 °C
1.2: 1 h
2.1: potassium carbonate / propan-1-ol / 24 h / Reflux
View Scheme
Multi-step reaction with 2 steps
1: o-xylene / 6 h / Reflux
2: potassium carbonate / propan-1-ol / 24 h / Reflux
View Scheme
3-amino-4-methyl benzoic acid methyl ester
18595-18-1

3-amino-4-methyl benzoic acid methyl ester

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydrogenchloride / ethanol; water / 6 h / 25 - 85 °C / Inert atmosphere
1.2: 0.75 h / 0 - 5 °C
2.1: sodium hydroxide / butan-1-ol / 12 h / Inert atmosphere; Reflux
2.2: 0.33 h / 25 - 125 °C
2.3: 1 h / 25 - 35 °C
View Scheme
Multi-step reaction with 3 steps
1.1: nitric acid / water; butan-1-ol / 16 h / Heating / reflux
2.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
3.1: sodium hydroxide; water; butan-1-ol / 0.5 h / Heating / reflux
3.2: 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: nitric acid / water; butan-1-ol
1.2: 16 h / Heating / reflux
2.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
3.1: sodium hydroxide; water / butan-1-ol / 0.5 h / Heating / reflux
3.2: 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sulfuric acid / ethanol / 8 h / 70 °C
2: potassium hydroxide / propan-1-ol / 17 °C / Reflux
3: potassium hydroxide; water / 60 °C
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / methanol; dichloromethane / 24 h / 40 °C
2: dichloromethane / 12 h / 20 °C
3: sodium hydroxide / 36 h / 110 - 120 °C
4: lithium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C
View Scheme
3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate
1025716-99-7

3-[(aminoiminomethyl)amino]-4-methylbenzoic acid methylester mononitrate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
2.1: sodium hydroxide; water; butan-1-ol / 0.5 h / Heating / reflux
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
2.1: sodium hydroxide; water / butan-1-ol / 0.5 h / Heating / reflux
2.2: 20 °C
View Scheme
3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one
55314-16-4, 75415-01-9, 123367-26-0

3-(N,N-dimethylamino)-1-(pyridin-3-yl)prop-2-en-1-one

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
2.1: sodium hydroxide; water; butan-1-ol / 0.5 h / Heating / reflux
2.2: 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: sodium hydroxide / butan-1-ol / 12 h / Heating / reflux
2.1: sodium hydroxide; water / butan-1-ol / 0.5 h / Heating / reflux
2.2: 20 °C
View Scheme
Multi-step reaction with 3 steps
1: sodium hydroxide / tert-butyl alcohol / 85 °C
2: copper(l) iodide; potassium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere
3: sodium hydroxide / ethanol; water / 2 h / 45 °C
View Scheme
Multi-step reaction with 2 steps
1: potassium carbonate / propan-1-ol / 24 h / Reflux
2: sodium hydroxide / dichloromethane; methanol / 20 °C
View Scheme
3-bromo-4-methylbenzoic acid
7697-26-9

3-bromo-4-methylbenzoic acid

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: sulfuric acid / 5 h / 75 °C
2: copper(l) iodide; potassium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere
3: sodium hydroxide / ethanol; water / 2 h / 45 °C
View Scheme
ethyl 3-bromo-4-methylbenzoate
147962-81-0

ethyl 3-bromo-4-methylbenzoate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere
2: sodium hydroxide / ethanol; water / 2 h / 45 °C
View Scheme
4-pyridin-3-ylpyrimidin-2-ylamine
66521-66-2

4-pyridin-3-ylpyrimidin-2-ylamine

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: copper(l) iodide; potassium iodide; potassium carbonate; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 20 h / 100 °C / Inert atmosphere
2: sodium hydroxide / ethanol; water / 2 h / 45 °C
View Scheme
C11H15N3O2*ClH

C11H15N3O2*ClH

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / propan-1-ol / 24 h / Reflux
2: sodium hydroxide / dichloromethane; methanol / 20 °C
View Scheme
3-pyridylboronic acid
1692-25-7

3-pyridylboronic acid

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / tetrahydrofuran; water / 12 h / 85 °C / Inert atmosphere
2: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere
3: sodium hydroxide; water / ethanol / 5 h / 100 °C
View Scheme
2-chloro-4-(pyridin-3-yl)pyrimidine
483324-01-2

2-chloro-4-(pyridin-3-yl)pyrimidine

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate; tris-(dibenzylideneacetone)dipalladium(0); 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl / 1,4-dioxane / 100 °C / Inert atmosphere
2: sodium hydroxide; water / ethanol / 5 h / 100 °C
View Scheme
5-cyano-2-methylaniline
60710-80-7

5-cyano-2-methylaniline

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: triethylamine / methanol; dichloromethane / 24 h / 50 °C
2: dichloromethane / 12 h / 20 °C
3: sodium hydroxide / butan-1-ol / 24 h / 120 °C
4: sodium hydroxide; water / ethanol / 5 h / 100 °C
View Scheme
methyl 3-(2,3-bis( tert-butoxycarbonyl)guanidino)-4-methylbenzonitrile

methyl 3-(2,3-bis( tert-butoxycarbonyl)guanidino)-4-methylbenzonitrile

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 12 h / 20 °C
2: sodium hydroxide / butan-1-ol / 24 h / 120 °C
3: sodium hydroxide; water / ethanol / 5 h / 100 °C
View Scheme
1-(5-cyano-2-methylphenyl)guanidine trifluoroacetate

1-(5-cyano-2-methylphenyl)guanidine trifluoroacetate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / butan-1-ol / 24 h / 120 °C
2: sodium hydroxide; water / ethanol / 5 h / 100 °C
View Scheme
methyl-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-4-methylbenzoate

methyl-3-(2,3-bis(tert-butoxycarbonyl)guanidino)-4-methylbenzoate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: dichloromethane / 12 h / 20 °C
2: sodium hydroxide / 36 h / 110 - 120 °C
3: lithium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C
View Scheme
methyl 3-guanidino-4-methylbenzoate trifluoroacetate

methyl 3-guanidino-4-methylbenzoate trifluoroacetate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: sodium hydroxide / 36 h / 110 - 120 °C
2: lithium hydroxide; water / methanol; tetrahydrofuran / 12 h / 20 °C
View Scheme
ethyl 4-methyl-3-nitro-benzoate
19013-15-1

ethyl 4-methyl-3-nitro-benzoate

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: palladium 10% on activated carbon; ammonium formate / methanol / Heating
2.1: hydrogenchloride / toluene; ethanol; water / Reflux
2.2: 1 h / 5 - 10 °C
3.1: sodium hydroxide / iso-butanol / Reflux
4.1: sodium hydroxide; water; ethanol / 45 - 50 °C
View Scheme
4-methyl-3-nitrobenzoic acid
96-98-0

4-methyl-3-nitrobenzoic acid

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: p-Toluic acid / toluene / Reflux
2.1: palladium 10% on activated carbon; ammonium formate / methanol / Heating
3.1: hydrogenchloride / toluene; ethanol; water / Reflux
3.2: 1 h / 5 - 10 °C
4.1: sodium hydroxide / iso-butanol / Reflux
5.1: sodium hydroxide; water; ethanol / 45 - 50 °C
View Scheme
3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline
641571-11-1

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

nilotinib
641571-10-0

nilotinib

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.25h;
Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 3h; Product distribution / selectivity;		94%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.25h;
Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 3h;
Stage #3: With sodium hydroxide In 1-methyl-pyrrolidin-2-one; water at 80℃; pH=11 - 12; Product distribution / selectivity;		94%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In 1-methyl-pyrrolidin-2-one at 60℃; for 1.5h;
Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In 1-methyl-pyrrolidin-2-one at 90℃; for 0.5h;		90%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

2-(trifluoromethyl)-1,4-phenylenediamine
364-13-6

2-(trifluoromethyl)-1,4-phenylenediamine

C24H19F3N6O
1089725-67-6

C24H19F3N6O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine In tetrahydrofuran for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: 2-(trifluoromethyl)-1,4-phenylenediamine In tetrahydrofuran at 0 - 20℃; for 24.5h; Inert atmosphere;		93%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

C12H10F3N3O2

C12H10F3N3O2

C29H22F3N7O3

C29H22F3N7O3

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In N,N-dimethyl-formamide92%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

N-methyl-N-methoxy-4-methyl-3-[(4-pyridin-3-yl-pyrimidin-2-yl)amino]benzamide

N-methyl-N-methoxy-4-methyl-3-[(4-pyridin-3-yl-pyrimidin-2-yl)amino]benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0℃; for 0.5h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 6h;		89.52%
With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride at 20℃; for 6h;60%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

tert-butyl alcohol
75-65-0

tert-butyl alcohol

tert-butyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

tert-butyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

Conditions
ConditionsYield
With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h;87%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline hydrochloride
917391-26-5

3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline hydrochloride

nilotinib
641571-10-0

nilotinib

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride at 45 - 50℃; for 2h;
Stage #2: 3-(4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline hydrochloride With sodium hydroxide In water at 25 - 30℃; for 2h; pH=8 - 9;		85%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

(2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine

(2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine

N-(6-((2S,6R)-2,6-dimethylmorpholin-4-yl)pyridin-3-yl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

N-(6-((2S,6R)-2,6-dimethylmorpholin-4-yl)pyridin-3-yl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: (2S,6R)-2,6-dimethyl-4-(5-aminopyridin-2-yl)morpholine In N,N-dimethyl-formamide at 0 - 25℃; for 12h;		78%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

benzyl alcohol
100-51-6

benzyl alcohol

benzyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

benzyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h;
Stage #2: benzyl alcohol for 12h; Reflux;		72%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-(4-ethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-(4-ethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

C29H24F3N7O

C29H24F3N7O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In toluene at 80℃; for 5h;
Stage #2: 3-(4-ethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In acetonitrile at 80℃; for 7h;		69%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

Propargylamine
2450-71-7

Propargylamine

4-methyl-N-(prop-2-ynyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)benzamide
1204575-26-7

4-methyl-N-(prop-2-ynyl-3-(4-pyridin-3-yl)pyrimidin-2-ylamino)benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide for 0.0833333h;
Stage #2: Propargylamine In N,N-dimethyl-formamide for 2h;		67%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-(3-oxo-4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-(3-oxo-4-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

4-methyl-3-([4-(3-pyridyl)-2-pyrimidinyl]amino)-N-[5-(3-oxo-4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide

4-methyl-3-([4-(3-pyridyl)-2-pyrimidinyl]amino)-N-[5-(3-oxo-4-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide

Conditions
ConditionsYield
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; 1,8-diazabicyclo[5.4.0]undec-7-ene In N,N-dimethyl-formamide at 20 - 60℃; for 24h; Inert atmosphere;65%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

2,4-dimethoxylbenzyl alcohol
7314-44-5

2,4-dimethoxylbenzyl alcohol

2,4-dimethoxybenzyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

2,4-dimethoxybenzyl (4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)carbamate

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h;
Stage #2: 2,4-dimethoxylbenzyl alcohol In toluene for 12h; Reflux;		63%
3-(5-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-(5-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-N-[5-(5-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide

4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]-N-[5-(5-methyl-1H-imidazol-1-yl)-3-(trifluoromethyl)phenyl]benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In acetonitrile at 80℃; for 5h;
Stage #2: 3-(5-methyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In acetonitrile at 60℃; for 4h;		61%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine
152460-10-1

6-methyl-1-N-(4-(pyridin-3-yl)pyrimidin-2-yl)benzene-1,3-diamine

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With diphenyl phosphoryl azide; triethylamine In toluene at 100℃; for 12h; Curtius Rearrangement;
Stage #2: With hydrogenchloride In water; toluene at 100℃;		60%
Multi-step reaction with 2 steps
1: diphenyl phosphoryl azide; triethylamine / toluene / 12 h / 100 °C
2: trifluoroacetic acid / dichloromethane / 8 h
View Scheme
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-(2,4-dimethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

3-(2,4-dimethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline

C29H24F3N7O

C29H24F3N7O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With oxalyl dichloride In tetrahydrofuran at 60℃; for 6h;
Stage #2: 3-(2,4-dimethyl-1H-imidazol-1-yl)-5-(trifluoromethyl)aniline In toluene at 70℃; for 6h;		59%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-(1H-imidazol-1-yl)-5-(trifluoromethyl)benzenamine
943320-48-7

3-(1H-imidazol-1-yl)-5-(trifluoromethyl)benzenamine

C27H20F3N7O

C27H20F3N7O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride at 70℃; for 6h;
Stage #2: 3-(1H-imidazol-1-yl)-5-(trifluoromethyl)benzenamine at 90℃; for 4h;		56%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

4-Aminobenzonitrile
873-74-5

4-Aminobenzonitrile

N-(4-cyanophenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

N-(4-cyanophenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 4-Aminobenzonitrile In N,N-dimethyl-formamide at 0 - 20℃; for 12h;		37%
4-HYDROXYPIPERIDINE
5382-16-1

4-HYDROXYPIPERIDINE

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

(4-hydroxypiperidin-1-yl)(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)methanone

(4-hydroxypiperidin-1-yl)(4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)phenyl)methanone

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 1h;
Stage #2: 4-HYDROXYPIPERIDINE In N,N-dimethyl-formamide at 0 - 20℃; for 12h;		37%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

4-Chloro-3-nitroaniline
635-22-3

4-Chloro-3-nitroaniline

4-methyl-N-(4-chloro-3-nitrophenyl)-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide

4-methyl-N-(4-chloro-3-nitrophenyl)-3-[(4-pyridin-3-ylpyrimidin-2-yl)amino]benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide for 0.5h; Inert atmosphere; Cooling with ice;
Stage #2: 4-Chloro-3-nitroaniline In N,N-dimethyl-formamide at 20 - 90℃; for 27h; Inert atmosphere;		36%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

1-[(2-iodo-4-aminophenyl)methyl]-4-methyl-piperazine

1-[(2-iodo-4-aminophenyl)methyl]-4-methyl-piperazine

C29H30IN7O

C29H30IN7O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride; N,N-dimethyl-formamide In N,N-dimethyl-formamide at 20℃; for 17h;
Stage #2: 1-[(2-iodo-4-aminophenyl)methyl]-4-methyl-piperazine With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2h;		33%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

[3-bromo-5-(trifluoromethyl)phenyl]amine
54962-75-3

[3-bromo-5-(trifluoromethyl)phenyl]amine

N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide
1205540-16-4

N-(3-bromo-5-(trifluoromethyl)phenyl)-4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzamide

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 25℃; for 3h;
Stage #2: [3-bromo-5-(trifluoromethyl)phenyl]amine In N,N-dimethyl-formamide at 80℃; for 18h;		29%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide
Stage #2: [3-bromo-5-(trifluoromethyl)phenyl]amine In N,N-dimethyl-formamide at 80℃; for 18h;		29%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

3-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]imidazol-1-yl]-5-(trifluoromethyl)aniline

3-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]imidazol-1-yl]-5-(trifluoromethyl)aniline

C34H36F3N7O2Si

C34H36F3N7O2Si

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In N,N-dimethyl-formamide27%
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With 2,4,6-trichlorobenzoyl chloride; triethylamine In tetrahydrofuran at 20℃; for 2h;
Stage #2: 3-[4-[[tert-butyl(dimethyl)silyl]oxymethyl]imidazol-1-yl]-5-(trifluoromethyl)aniline With dmap In tetrahydrofuran at 20℃; for 10h;		700 mg
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

1-[(2-bromo-4-aminophenyl)methyl]-4-methyl-piperazine
859027-13-7

1-[(2-bromo-4-aminophenyl)methyl]-4-methyl-piperazine

C29H30BrN7O

C29H30BrN7O

Conditions
ConditionsYield
Stage #1: 4-methyl-3-{[4-(pyridin-3-yl)pyrimidin-2-yl]amino}benzoic acid With thionyl chloride In N,N-dimethyl-formamide at 20℃; for 17h;
Stage #2: 3-bromo-4-(4-methyl-piperazin-1-ylmethyl)-phenylamine With dmap; N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃; for 2.5h;		25%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

6-(piperazin-1-yl)pyridin-3-ol
287114-37-8

6-(piperazin-1-yl)pyridin-3-ol

[4-(5-hydroxypyridin-2-yl)piperazin-1-yl][4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]methanone

[4-(5-hydroxypyridin-2-yl)piperazin-1-yl][4-methyl-3-(4-pyridin-3-ylpyrimidin-2-ylamino)phenyl]methanone

Conditions
ConditionsYield
With triethylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 0 - 5℃; for 1h;20%
4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid
641569-94-0

4-methyl-3-((4-(pyridin-3-yl)pyrimidin-2-yl)amino)benzoic acid

furan-2-ylmethanamine
617-89-0

furan-2-ylmethanamine

N-(2-furanylmethyl)-4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzamide

N-(2-furanylmethyl)-4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzamide

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In DMF (N,N-dimethyl-formamide) at 20℃; for 24.3333h;

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid Chemical Properties

Molecular Structure of 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (CAS NO.641569-94-0):
Product Name: 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid
Molecular Formula: C17H14N4O2
Molecular Weight: 306.32 g/mol
Canonical SMILES: O=C(O)c1cc(c(cc1)C)Nc2nc(ccn2)c3cccnc3
InChI: InChI=1/C17H14N4O2/c1-11-4-5-12(16(22)23)9-15(11)21-17-19-8-6-14(20-17)13-3-2-7-18-10-13/h2-10H,1H3,(H,22,23)(H,19,20,21)
Mol File: 641569-94-0.mol
Nominal Mass: 306
Average Mass: 306.3187
Monoisotopic Mass: 306.111676
H bond acceptors: 6
H bond donors: 2
Freely Rotating Bonds: 3
Polar Surface Area: 88
Index of Refraction: 1.676
Molar Refractivity: 86.248 cm3
Molar Volume: 229.235 cm3
Polarizability: 34.191×10-24cm3
Surface Tension: 67.142 dyne/cm
Density: 1.336 g/cm3
Flash Point: 309.367 °C
Enthalpy of Vaporization: 92.317 kJ/mol
Boiling Point: 587.927 °C at 760 mmHg
Vapour Pressure: 0 mmHg at 25 °C

4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid Specification

 4-Methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]benzoic acid (CAS NO.641569-94-0), its Synonyms are 4-Methyl-3-[[4-(pyridin-3-yl)pyrimidin-2-yl]amino]benzoic acid ; 4-methyl-3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]- .

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