4-Chloropyrrolo[2,3-d]pyrimidine supplier

Name
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
EINECS 628-079-2
CAS No. 3680-69-1
Article Data55
CAS DataBase
Density 1.531 g/cm³
Solubility
Melting Point 183-184 °C
Formula C₆H₄ClN₃
Boiling Point 325.9 °C at 760 mmHg
Molecular Weight 153.571
Flash Point 180.7 °C
Transport Information UN 2811 6.1/PG 3
Appearance light brown to brown crystalline powder
Safety 26-37-45-36
Risk Codes 36/37/38-25-20/21/22
Molecular Structure
Hazard Symbols Xi,T,Xn
Synonyms 1H-Pyrrolo[2,3-d]pyrimidine,4-chloro- (7CI,9CI);4-Chloro-7H-pyrrolo[2,3-d]pyrimidine;6-Chloro-7-deazapurine;NSC 64952;7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-;4-Chloropyrrolo[2,3-d]pyrimidine;
PSA 41.57000
LogP 1.61130

Synthetic route

: 3680-71-5
Allopurinol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With chlorine In 1-methyl-pyrrolidin-2-one; toluene at 160 - 180℃; Temperature;	95%
With 1,2,3-trichloropropane; chlorine In 1-methyl-pyrrolidin-2-one; toluene Reflux;	95%
With dmap; bis(trichloromethyl) carbonate In chlorobenzene at 50 - 60℃; for 6h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	94.2%

: 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; water at 20℃; for 7.5h; Reflux;	94%
Stage #1: 6-chloro-5-(2-methoxyvinyl)pyrimidin-4-ylamine With hydrogenchloride; water In tetrahydrofuran at 20℃; Reflux; Stage #2: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1h;
With hydrogenchloride In tetrahydrofuran; water for 7.5h; Reflux;	54.5 g

: 3680-71-5
7-deazahypoxanthine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate for 2h; Reflux;	93%
With trichlorophosphate	92%
With trichlorophosphate for 4h; Reflux;	91%

: 4-hydroxypyrrolo[2,3-D]pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate for 3h; Reflux;	93%

: 4-amino-6-chloro-5-(2,2-diethoxyethyl)pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With hydrogenchloride In water at 50℃; for 4h; Reagent/catalyst;	92%
With hydrogenchloride; water In Petroleum ether at 50℃; for 4h;	91%

: 4-amino-6-chloropyrimidine-5-acetaldehyde

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water at 50℃; for 3h; Concentration; Temperature; Industrial scale;	91.4%
With hydrogenchloride In methanol; water at 50 - 60℃; for 3h;	82%
With acetic acid at 20℃; for 14h;	26.1 g

: 1,1-dichloro-2-cyano-4-methoxy-1,3-butadiene

: 6313-33-3
formamidine hydrochloride

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With sodium methylate In methanol at 25 - 70℃; for 10h;	91%

: 1,1-dichloro-2-cyano-4-methoxy-1,3-butadiene

: 3473-63-0
formamidine acetic acid

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With sodium methylate In methanol at 30 - 70℃; for 10h;	90.2%

: 123148-78-7
4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With potassium benzo[d][1,3]dioxol-5-yltrifluoroborate; PdCl2(1,1'-bis(diphenylphosphino)ferrocene); triethylamine In ethanol; dichloromethane for 19h; Reagent/catalyst; Reflux;	90%

: 3680-71-5
1H-pyrrolo[2,3-d]pyrimidin-4(7H)-one

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate at 100℃; for 5h;	65.7%
With trichlorophosphate for 5h; Reflux;	54%
With trichlorophosphate for 5h; Reflux;	54%
With trichlorophosphate for 5h; Reflux;	54%

: 16019-33-3
2-(4,6-dichloropyrimidin-5-yl)acetaldehyde

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With ammonium hydroxide at 60 - 70℃; for 24h;	34%
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / ethanol / 2 h / 40 °C 2: ammonium hydroxide / ethanol / 20 h / 70 °C 3: hydrogenchloride; water / Petroleum ether / 4 h / 50 °C View Scheme
Multi-step reaction with 3 steps 1: toluene-4-sulfonic acid / ethanol / 3 h / 40 °C 2: ammonium hydroxide / 3 h / 60 °C 3: hydrogenchloride / water / 4 h / 50 °C View Scheme

: 52133-67-2
ethyl 2-cyano-4,4-diethoxybutyrate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 64 percent / NaOEt 2: 92 percent / aq. HCl 3: 81 percent / H2 / Raney Ni 4: 66 percent / POCl3 View Scheme
Multi-step reaction with 3 steps 1: NaOEt / ethanol 2: 1.) Raney-Nickel; 2.) HCl 3: POCl3 View Scheme
Multi-step reaction with 4 steps 1: 64 percent / EtONa / dimethylformamide; ethanol / 6 h / Heating 2: aq. NH3 / Raney nickel / 6 h / Heating 3: 86 percent / 1N aq. HCl / 1 h / 20 °C 4: 79 percent / POCl3 / 1.5 h / Heating View Scheme

: 7400-05-7
6-amino-5-(2,2-diethoxyethyl)-2-thioxo-2,3-dihydropyrimidin-4(1H)-one

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 92 percent / aq. HCl 2: 81 percent / H2 / Raney Ni 3: 66 percent / POCl3 View Scheme
Multi-step reaction with 3 steps 1: aq. NH3 / Raney nickel / 6 h / Heating 2: 86 percent / 1N aq. HCl / 1 h / 20 °C 3: 79 percent / POCl3 / 1.5 h / Heating View Scheme
Multi-step reaction with 3 steps 1: hydrogenchloride / water / 22 h 2: ammonium hydroxide / water / 72 h / Reflux 3: trichlorophosphate / 5 h / Reflux View Scheme
Multi-step reaction with 3 steps 1.1: hydrogenchloride / water 2.1: ammonium hydroxide / water 2.2: raney nickel / 5 h / 100 °C 3.1: trichlorophosphate / 5 h / 100 °C View Scheme

: 67831-84-9
2-thioxo-1,2,3,7-tetrahydro-4H-pyrrolo[2,3-d]pyrimidin-4-one

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 81 percent / H2 / Raney Ni 2: 66 percent / POCl3 View Scheme
Multi-step reaction with 2 steps 1: ammonium hydroxide / water / 72 h / Reflux 2: trichlorophosphate / 5 h / Reflux View Scheme
Multi-step reaction with 2 steps 1.1: ammonium hydroxide / water 1.2: raney nickel / 5 h / 100 °C 2.1: trichlorophosphate / 5 h / 100 °C View Scheme

: 7400-05-7
6-amino-5-(2,2-diethoxy)-2-mercaptopyrimidine-4-ol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) Raney-Nickel; 2.) HCl 2: POCl3 View Scheme
Multi-step reaction with 3 steps 1: ammonia / nickel / water / 90 °C 2: hydrogenchloride; water / 2.5 h / 20 °C 3: trichlorophosphate / 2.5 h / 100 °C View Scheme
Multi-step reaction with 3 steps 1: nickel / water / 1 h / Heating / reflux 3: trichlorophosphate / 1.5 h / Heating / reflux View Scheme

: 7400-06-8
4-amino-6-hydroxy-5-(2,2-diethoxyethyl)pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 86 percent / 1N aq. HCl / 1 h / 20 °C 2: 79 percent / POCl3 / 1.5 h / Heating View Scheme

: 3680-71-5
7-deazahypoxanthine

A 4-CHLORO-5,7-DIHYDRO-PYRROLO[2,3-D]PYRMIDIN-6-ONE: 4-CHLORO-5,7-DIHYDRO-PYRROLO[2,3-D]PYRMIDIN-6-ONE

B: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With trichlorophosphate	A 49 mg (70%) B n/a

: 7400-06-8
6-amino-5-(2,2-diethoxyethyl)pyrimidin-4-ol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 2.5 h / 20 °C 2: trichlorophosphate / 2.5 h / 100 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 4 h / 25 - 30 °C 2: trichlorophosphate / 1 h / 100 - 105 °C View Scheme
Multi-step reaction with 2 steps 1: hydrogenchloride; water / 2.5 h / 20 °C 2: trichlorophosphate / 2.5 h / 100 °C View Scheme
Multi-step reaction with 2 steps 2: trichlorophosphate / 1.5 h / Heating / reflux View Scheme

: 6-amino-5-(2,2-diethoxyethyl)-2-mercaptopyrimidin-4-ol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonia / water / 90 °C 2: hydrogenchloride / water / 2.5 h / 20 °C 3: trichlorophosphate / 2.5 h / 100 °C / Inert atmosphere View Scheme

: 1615680-91-5
6-chloro-5-((trimethylsilyl)ethynyl)pyrimidin-4-amine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; potassium tert-butylate at 90℃; for 0.833333h;	505 mg

: 16019-31-1
5-allyl-4,6-dichloropyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: ammonium hydroxide / ethanol / 24 h / 60 °C / Industrial scale 2: ozone / methanol / -30 °C / Industrial scale 3: hydrogenchloride / methanol; water / 3 h / 50 °C / Industrial scale View Scheme
Multi-step reaction with 2 steps 1: ozone / methanol; dichloromethane / 2 h / -40 °C 2: ammonium hydroxide / 24 h / 60 - 70 °C View Scheme
Multi-step reaction with 3 steps 1: ammonium hydroxide / ethanol / 24 h / 70 °C / Sealed tube 2: triethylamine; dimethyl sulfoxide; ozone / methanol / 2 h / -5 - 0 °C 3: acetic acid / 14 h / 20 °C View Scheme

: 773076-83-8
2-cyano-4,4-dimethoxybutyric acid ethyl ester

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium ethanolate / ethanol / Reflux 2: hydrogenchloride / water / 45 °C 3: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 50 °C View Scheme

: 6-amino-5-(2,2-dimethoxyethyl)pyrimidin-4-ol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogenchloride / water / 45 °C 2: trichlorophosphate; N-ethyl-N,N-diisopropylamine / toluene / 50 °C View Scheme

: 16019-30-0
5-(prop-2-en-1-yl)pyrimidine-4,6-diol

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: ozone / methanol; dichloromethane / 2 h / -40 °C 3: ammonium hydroxide / 24 h / 60 - 70 °C View Scheme
Multi-step reaction with 4 steps 1: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: ammonium hydroxide / ethanol / 24 h / 70 °C / Sealed tube 3: triethylamine; dimethyl sulfoxide; ozone / methanol / 2 h / -5 - 0 °C 4: acetic acid / 14 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 2: ozone / methanol; dichloromethane / 2 h / -40 °C 3: toluene-4-sulfonic acid / ethanol / 2 h / 40 °C 4: ammonium hydroxide / ethanol / 20 h / 70 °C 5: hydrogenchloride; water / Petroleum ether / 4 h / 50 °C View Scheme

: 14052-82-5
4,6-dichloro-5-(2,2-diethoxyethyl)pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: ammonium hydroxide / ethanol / 20 h / 70 °C 2: hydrogenchloride; water / Petroleum ether / 4 h / 50 °C View Scheme

: 40637-56-7
dimethyl allylmalonate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: sodium methylate / methanol / 5 h / 0 - 60 °C 2: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 3: ozone / methanol; dichloromethane / 2 h / -40 °C 4: ammonium hydroxide / 24 h / 60 - 70 °C View Scheme
Multi-step reaction with 5 steps 1: sodium methylate / methanol / 5 h / 0 - 60 °C 2: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 3: ammonium hydroxide / ethanol / 24 h / 70 °C / Sealed tube 4: triethylamine; dimethyl sulfoxide; ozone / methanol / 2 h / -5 - 0 °C 5: acetic acid / 14 h / 20 °C View Scheme
Multi-step reaction with 6 steps 1: sodium methylate / methanol / 5 h / 0 - 60 °C 2: N,N-dimethyl-aniline; trichlorophosphate / acetonitrile / 3 h / 80 °C / Inert atmosphere 3: ozone / methanol; dichloromethane / 2 h / -40 °C 4: toluene-4-sulfonic acid / ethanol / 2 h / 40 °C 5: ammonium hydroxide / ethanol / 20 h / 70 °C 6: hydrogenchloride; water / Petroleum ether / 4 h / 50 °C View Scheme

: 67831-84-9
2-mercapto-4-hydroxy-7H-pyrrolo[2,3-d]pyrimidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: sodium hydroxide; dihydrogen peroxide / water / 2 h / 15 - 20 °C 2: hydrogenchloride / water / 1 h 3: trichlorophosphate / 85 °C View Scheme

: C10H19N3O3S

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogenchloride / water / 20 °C / pH 2 - 3 2: sodium hydroxide; dihydrogen peroxide / water / 2 h / 15 - 20 °C 3: hydrogenchloride / water / 1 h 4: trichlorophosphate / 85 °C View Scheme

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 74-89-5
methylamine

: 78727-16-9
4-(methylamino)-7H-pyrrolo<2,3-d>pyrimidine

Conditions

Conditions	Yield
In ethanol at 100℃; for 2h; Sealed tube;	100%
With hydrogenchloride In methanol for 6h; Heating;	85%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 123148-78-7
4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide	100%
With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide	100%
With N-iodo-succinimide; sodium sulfate In ethanol; N,N-dimethyl-formamide	100%

: 916177-00-9
(5-(methoxycarbonyl)-1-tosyl-1H-pyrrol-3-yl)boronic acid

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 170℃; for 0.166667h; Microwave irradiation;	100%

: 956460-98-3
4-tert-butoxycarbonylamino-piperidine-4-carboxylic acid ethyl ester

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 956460-97-2
4-tert-butoxycarbonylamino-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperidine-4-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 68h;	100%
With triethylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 68h;	100%
With triethylamine In 1-methyl-pyrrolidin-2-one at 110℃; for 68h;	100%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 870706-50-6
4-chloro-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78 - 20℃; for 5.5h; Stage #2: With water; ammonium chloride In tetrahydrofuran; hexane	100%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 1100318-96-4
4-iodo-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With hydrogen iodide In water at 20℃; for 80h; Inert atmosphere;	100%
With hydrogen iodide at 20℃; for 80h; Inert atmosphere;	98%
With hydrogen iodide In water at 20℃; for 48h;	91%

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 941685-26-3
4-chloro-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrole[2,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide Cooling with ice;	100%
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide at 20℃; for 1h; Cooling with ice; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide for 1h; Cooling with ice;	100%
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 10℃; for 1h; Cooling with ice; Inert atmosphere; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 10 - 20℃;	97%

: 13154-24-0
triisopropylsilyl chloride

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 870706-50-6
4-chloro-7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 1h; Inert atmosphere; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; hexane at -78 - 20℃; for 4.5h; Inert atmosphere;	100%
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 6.8℃; for 0.916667h; Inert atmosphere; Stage #2: triisopropylsilyl chloride In tetrahydrofuran; mineral oil at 0℃; for 4h; Inert atmosphere; Reflux;	99%

: 942185-01-5
1H-pyrazolo[3,4-b]pyridin-5-amine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: N-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazolo[3,4-b]pyridin-5-amine

Conditions

Conditions	Yield
With hydrogenchloride In ethanol; water for 6h; Reflux;	100%

: (+/-)-cis-4-methyl-1-(phenylmethyl)-piperidin-3-ylamine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: cis-1-benzyl-4-methyl-N-{7H-pyrrolo[2,3-d]pyrimidin-4-yl}piperidin-3-amine

Conditions

Conditions	Yield
With potassium carbonate In water at 100℃; for 48h; Sealed tube;	100%

: 309956-78-3
(R)-piperidin-3-ylcarbamic acid tert-butyl ester

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: (R)-tert-butyl (1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl)carbamate

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 80℃; for 52h; Inert atmosphere; Sealed tube;	100%

: tert-butyl N-methyl-N-[(3R,4R)-4-methylpiperidin-3-yl]carbamate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: C18H27N5O2

Conditions

Conditions	Yield
With potassium carbonate In 1,4-dioxane; water at 100℃; for 10h;	100%

: (R)-N-methyl-5-((R)-1-phenylethyl)-5-azaspiro[2.4]heptan-7-amine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: N-methyl-N-((R)-5-((R)-1-phenylethyl)-5-azaspiro[2.4]heptan-7-yl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Conditions

Conditions	Yield
With potassium carbonate In water for 18h; Reflux;	100%

: benzyl (3S,4R)-3-methyl-1,6-diazaspiro[3.4]octane-1-carboxylate oxalate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: benzyl (3S,4R)-3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.4]octane-1-carboxylate

Conditions

Conditions	Yield
With potassium phosphate In ethanol; water at 40 - 80℃; for 5h; Inert atmosphere;	100%
With potassium phosphate In ethanol; water at 80℃; for 5h; Inert atmosphere;
With potassium phosphate In ethanol; water at 80℃; for 5h; Temperature; Inert atmosphere;

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 22276-95-5
5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With N-Bromosuccinimide In acetonitrile at 100℃; for 0.166667h; microwave irradiation;	99%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 12h;	95%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 72h;	95%

: 100-60-7
N-methylcyclohexylamine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 252722-30-8
N-cyclohexyl-N-methyl-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Conditions

Conditions	Yield
In 1,4-dioxane at 110℃; for 9h; Microwave irradiation; Sealed tube;	99%
Stage #1: N-methylcyclohexylamine; 4-chloro-1H-pyrrolo[2,3-d]pyrimidine In tert-butyl alcohol at 100℃; for 24h; Stage #2: With hydrogenchloride In water; tert-butyl alcohol pH=1; Stage #3: With sodium hydroxide In water; tert-butyl alcohol pH=14;	88%
In tert-butyl alcohol at 85℃;

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 57260-71-6
1-t-Butoxycarbonylpiperazine

: 4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperazine-1-carboxylic acid tert-butyl ester

Conditions

Conditions	Yield
With RuPhos palladacycle; lithium hexamethyldisilazane; ruphos In tetrahydrofuran at 65℃; for 4h; Inert atmosphere; Sealed vial;	99%
With triethylamine In butan-1-ol at 90℃;	74%
With triethylamine In N,N-dimethyl-formamide at 110℃; for 16h;	59%

: 1153949-15-5
tert-butyl 3-(cyanomethyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-1-carboxylate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 1,1-dimethylethyl 3-(cyanomethyl)-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]-1-azetidinecarboxylate

Conditions

Conditions	Yield
With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloro palladium(II); cesium fluoride In water; tert-butyl alcohol Suzuki Coupling; Inert atmosphere; Reflux;	99%
With [1,1′-bis(di-cyclohexylphosphino)ferrocene]dichloropalladium (II); cesium fluoride In water; tert-butyl alcohol Inert atmosphere; Reflux;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water for 1h; Reflux;

: 2-(1-(ethanesulfonyl)-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)azetidine-3-yl)acetonitrile

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 1187594-09-7
Baricitinib

Conditions

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80 - 85℃; for 5h;	99%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; toluene; tert-butyl alcohol at 100℃; for 48h; Concentration; Temperature; Solvent; Reagent/catalyst; Suzuki Coupling; Inert atmosphere;	90%
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran; water at 90℃; for 19h; Autoclave; Inert atmosphere;	90%
With tetrakis(triphenylphosphine) palladium(0); cesium fluoride In water; toluene; tert-butyl alcohol for 48h; Suzuki Coupling; Reflux; Inert atmosphere;	84%

: 960-16-7
tributylphenylstannane

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 1168106-39-5
4-phenyl-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With 1,8-Cineole; bis-triphenylphosphine-palladium(II) chloride; triphenyl-arsane at 100℃; for 32h; Stille Cross-Coupling (Migita-Kosugi-Stille Coupling);	99%

: t-butyl (3S,4R)-3-methyl-1,6-diazaspiro[3.4]octane-1-carboxylate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: t-butyl (3S,4R)-3-methyl-6-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,6-diazaspiro[3.4]octane-1-carboxylate

Conditions

Conditions	Yield
With potassium carbonate In water at 110℃; for 4h;	99%

: 18997-19-8
Chloromethyl pivalate

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 1146629-75-5
(4-chloro-7H-pyrrolo[2,3-d]pyrimidin-7-yl)methyl 2,2-dimethylpropanoate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 14h;	98.85%
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere; Stage #2: Chloromethyl pivalate In tetrahydrofuran at 0 - 20℃; Inert atmosphere;	91%
Stage #1: 4-chloro-1H-pyrrolo[2,3-d]pyrimidine With sodium hydride In tetrahydrofuran; mineral oil at 0 - 20℃; Inert atmosphere; Stage #2: Chloromethyl pivalate In tetrahydrofuran; mineral oil at 0 - 20℃; Product distribution / selectivity; Inert atmosphere;	91%

: 98-09-9
benzenesulfonyl chloride

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 186519-89-1
4-chloro-7-(phenylsulfonyl)-7H-pyrrolo [2,3-d]pyrimidine

Conditions

Conditions	Yield
With sodium hydride In tetrahydrofuran at 0 - 20℃;	98%
With sodium hydride at 0 - 25℃; for 4h;	98%
With sodium t-butanolate In tetrahydrofuran at 10 - 22℃; for 2h;	92%

: 110-89-4
piperidine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 94581-94-9
4-(piperidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 90℃;	98%
With potassium hydroxide In water at 100℃; under 750.075 Torr; for 0.166667h; Microwave irradiation;	84%
In tert-butyl alcohol at 85℃; for 3h;	60%
In tert-butyl alcohol at 100℃; for 0.166667h; Microwave irradiation;

: 367-21-5
3-chloro-4-fluorophenylamine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 346600-33-7
(3-chloro-4-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 90℃;	98%

: 57946-56-2
2-fluoro-4-chloroaniline

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 865364-20-1
(4-chloro-2-fluoro-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 90℃;	98%

: 54060-30-9
3-acetylenephenylamine

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 186519-85-7
(3-ethynyl-phenyl)-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-amine

Conditions

Conditions	Yield
With silver trifluoromethanesulfonate In N,N-dimethyl-formamide at 90℃;	98%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 271-70-5
7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In methanol under 760.051 Torr; for 16h;	98%
With ammonium formate; 20% Pd(OH)2 on carbon In methanol for 2h; Heating / reflux;	97%
With hydrogen; palladium on activated charcoal	84%
With ammonium hydroxide; hydrogen; palladium on activated charcoal In ethanol at 20℃; for 6h;	83.7%
With hydrogen; palladium 10% on activated carbon In methanol at 20℃;

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 98-59-9
p-toluenesulfonyl chloride

: 479633-63-1
4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

Conditions

Conditions	Yield
With sodium hydroxide In water; acetone at 0 - 20℃; for 6h;	97%
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 0.5h; Large scale;	97.7%
With dmap; triethylamine In dichloromethane at 0 - 20℃; Industrial scale;	97.7%

: 3680-69-1
4-chloro-1H-pyrrolo[2,3-d]pyrimidine

: 74-88-4
methyl iodide

: 7781-10-4
4-Chlor-7-methyl-7H-pyrrolo<2,3-d>pyrimidin

Conditions

Conditions	Yield
With sodium hydride In N,N-dimethyl-formamide at 20℃; for 4h;	97%
With caesium carbonate In DMF (N,N-dimethyl-formamide) at 20℃; for 1h;	94%
With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 6h;	88%

4-Chloropyrrolo[2,3-d]pyrimidine Chemical Properties

IUPAC Name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine
Systematic of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): 4-Chloropyrrolo(2,3-d)pyrimidine ; BRN 0607871 ; NSC 64952 ; 7H-Pyrrolo(2,3-d)pyrimidine, 4-chloro-
CAS NO: 3680-69-1
Classification Code: Drug / Therapeutic Agent
Molecular Formula of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): C₆H₄ClN₃
Molecular Weight: 153.5691
Molecular Structure:

ProductCategories: Heterocycles ; Heterocycles series ; Halides ; Pyrimidine ; Heterocyclic Compounds ; Biochemistry ; Nucleobases and their analogs ; Nucleosides, Nucleotides & Related Reagents ; CHIRAL CHEMICALS ; Naphthyridine,Quinoline ; Bases & Related Reagents ; Intermediates ; Nucleotides ; Fused Ring Systems ; Heterocyclic Building Blocks
Melting Point: 183-184°C
Polar Surface Area: 30.71 Å²
Index of Refraction: 1.72
Molar Refractivity: 39.6 cm³
Molar Volume: 100.2 cm³
Surface Tension: 74.7 dyne/cm
Density of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (CAS NO.3680-69-1): 1.531 g/cm³
Flash Point: 180.7 °C
Enthalpy of Vaporization: 54.55 kJ/mol
Boiling Point: 325.9 °C at 760 mmHg
Vapour Pressure: 0.000424 mmHg at 25°C

4-Chloropyrrolo[2,3-d]pyrimidine Toxicity Data With Reference

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	297mg/kg (297mg/kg)		Gann. Japanese Journal of Cancer Research. Vol. 56, Pg. 219, 1965.

4-Chloropyrrolo[2,3-d]pyrimidine Safety Profile

Hazard Codes: Irritant Xi, Toxic T,Xn
Risk Statements: 36/37/38-25-20/21/22
R36/37/38: Irritating to eyes, respiratory system and skin.
R25: Toxic if swallowed.
R20/21/22: Harmful by inhalation, in contact with skin and if swallowed.
Safety Statements: 26-37-45-36
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.
S37: Wear suitable gloves.
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)
S36: Wear suitable protective clothing.
RIDADR: UN 2811 6.1/PG 3
RTECS: UY9360000
HazardClass: IRRITANT

Product Name

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

Synthetic route

4-Chloropyrrolo[2,3-d]pyrimidine Chemical Properties

4-Chloropyrrolo[2,3-d]pyrimidine Toxicity Data With Reference

4-Chloropyrrolo[2,3-d]pyrimidine Safety Profile

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