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24391-41-1

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24391-41-1 Usage

General Description

4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile, also known as CAS Number 84905-80-6, is a synthetic organic compound belonging to the class of pyrrolopyrimidines. It's a specific type of heterocyclic aromatic organic compound consisting of a pyrrole and a pyrimidine ring fused together. 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile is known for its high reactivity due to the presence of both the chloro-group and the carbonitrile group. Although it does not have much direct use, it serves as a valuable building block in the chemical industry, often used in the synthesis of more complex molecules especially in medical, pharmaceutical and agrochemical research. The exact physical features, including boiling point, melting point, and solubility can vary based on different factors. The compound normally appears as a white to light yellow crystalline powder.

Check Digit Verification of cas no

The CAS Registry Mumber 24391-41-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 2,4,3,9 and 1 respectively; the second part has 2 digits, 4 and 1 respectively.
Calculate Digit Verification of CAS Registry Number 24391-41:
(7*2)+(6*4)+(5*3)+(4*9)+(3*1)+(2*4)+(1*1)=101
101 % 10 = 1
So 24391-41-1 is a valid CAS Registry Number.
InChI:InChI=1/C7H3ClN4/c8-6-5-4(1-9)2-10-7(5)12-3-11-6/h2-3H,(H,10,11,12)

24391-41-1SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 19, 2017

Revision Date: Aug 19, 2017

1.Identification

1.1 GHS Product identifier

Product name 4-CHLORO-7H-PYRROLO[2,3-D]PYRIMIDINE-5-CARBONITRILE

1.2 Other means of identification

Product number -
Other names 4-Chlor-5-cyan-7H-pyrrolo<2,3-d>pyrimidin

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:24391-41-1 SDS

24391-41-1Synthetic route

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime
908287-23-0

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 20℃;97%
With thionyl chloride In dichloromethane at 25 - 45℃;89.4%
With thionyl chloride In dichloromethane at 20 - 40℃; for 22h;77%
Stage #1: 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime With thionyl chloride In dichloromethane at 20℃;
Stage #2: With sodium hydrogencarbonate In water pH=4;
With thionyl chloride In dichloromethane at 20℃;
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With thionyl chloride In dichloromethane at 20 - 45℃;89.4%
5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
22276-95-5

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

4-tolyl thiocyanate
5285-74-5

4-tolyl thiocyanate

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With n-butyllithium In tetrahydrofuran; methanol; dichloromethane
4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine
123148-78-7

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

tri-n-butyltin cyanide
2179-92-2

tri-n-butyltin cyanide

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Stage #1: tri-n-butyltin cyanide; tetrakis(triphenylphosphine) palladium(0) In 1,1-dichloroethane for 0.5h; Inert atmosphere; Reflux;
Stage #2: 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine In 1,1-dichloroethane for 24h; Reflux; Inert atmosphere;
5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
22276-95-5

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

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C
2.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 20 °C
3.2: pH 4
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C
2.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 0.5 h / 20 °C
3.1: thionyl chloride / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 3 steps
1.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere
1.2: -78 - 20 °C
2.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h / 20 °C
3.1: thionyl chloride / dichloromethane / 20 °C
View Scheme
4-chloro-1H-pyrrolo[2,3-d]pyrimidine
3680-69-1

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

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C
3.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 1 h / 20 °C
4.1: thionyl chloride / dichloromethane / 20 °C
4.2: pH 4
View Scheme
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C
3.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 0.5 h / 20 °C
4.1: thionyl chloride / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: N-Bromosuccinimide / N,N-dimethyl-formamide / 1 h / 20 °C
2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C
View Scheme
Multi-step reaction with 4 steps
1.1: N-Bromosuccinimide / dichloromethane / 3 h / 20 °C / Inert atmosphere
2.1: n-butyllithium / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere
2.2: -78 - 20 °C
3.1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h / 20 °C
4.1: thionyl chloride / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 2 steps
1.1: N-iodo-succinimide / N,N-dimethyl-formamide / 20 °C
2.1: tetrakis(triphenylphosphine) palladium(0) / 1,1-dichloroethane / 0.5 h / Inert atmosphere; Reflux
2.2: 24 h / Reflux; Inert atmosphere
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxaldehyde

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxaldehyde

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 1 h / 20 °C
2.1: thionyl chloride / dichloromethane / 20 °C
2.2: pH 4
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium hydroxide / ethanol; water / 0.5 h / 20 °C
2: thionyl chloride / dichloromethane / 20 °C
View Scheme
Multi-step reaction with 2 steps
1: hydroxylamine hydrochloride; sodium hydroxide / water; ethanol / 1 h / 20 °C
2: thionyl chloride / dichloromethane / 20 °C
View Scheme
5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine
22276-95-5

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

P-toluenesulfonyl cyanide
19158-51-1

P-toluenesulfonyl cyanide

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Stage #1: 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine With n-butyllithium In tetrahydrofuran at -78℃; for 1h; Inert atmosphere;
Stage #2: P-toluenesulfonyl cyanide In tetrahydrofuran at -78 - 20℃;
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate
167484-18-6

benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate

benzyl 1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,2-dihydro-1'H-spiro[indole-3,4'-piperidine]-1'-carboxylate

benzyl 1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1,2-dihydro-1'H-spiro[indole-3,4'-piperidine]-1'-carboxylate

Conditions
ConditionsYield
With potassium dihydrogenphosphate; phosphoric acid In dimethyl sulfoxide at 80℃; for 12h;74%
With potassium dihydrogenphosphate; phosphoric acid In dimethyl sulfoxide at 80℃;
bromoacetic acid tert-butyl ester
5292-43-3

bromoacetic acid tert-butyl ester

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

tert-butyl 2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate

tert-butyl 2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate

Conditions
ConditionsYield
Stage #1: 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile With sodium hydride In N,N-dimethyl-formamide; mineral oil for 0.0833333h;
Stage #2: bromoacetic acid tert-butyl ester In N,N-dimethyl-formamide; mineral oil for 2h;
74%
(S)-3-phenyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride
1548339-56-5

(S)-3-phenyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-4-(2-(4-oxo-3-phenyl-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
1548331-43-6

(S)-4-(2-(4-oxo-3-phenyl-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With triethylamine In butan-1-ol for 1.5h; Reflux;64%
With triethylamine In butan-1-ol for 1.5h; Reflux;64%
With triethylamine In butan-1-ol for 1.5h; Reflux;
(S)-2-(azetidin-2-yl)-5-chloro-3-(2,2-difluoroethyl)pyrrolo[1,2-f][1,2,4] triazin4(3H)-one hydrochloride
1548339-64-5

(S)-2-(azetidin-2-yl)-5-chloro-3-(2,2-difluoroethyl)pyrrolo[1,2-f][1,2,4] triazin4(3H)-one hydrochloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-4-(2-(5-chloro-3-(2,2-difluoroethyl)-4-oxo-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)azetidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
1548333-77-2

(S)-4-(2-(5-chloro-3-(2,2-difluoroethyl)-4-oxo-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)azetidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With triethylamine In butan-1-ol at 130℃; for 2h;63%
With triethylamine In butan-1-ol at 130℃; for 2h;63%
With triethylamine In butan-1-ol at 130℃; for 2h;63%
(5)-7-fluoro-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride
1548341-37-2

(5)-7-fluoro-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-4-(2-(7-fiuoro-4-oxo-3,4-dihydropyrrolo[1,2-f][l,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
1548335-65-4

(S)-4-(2-(7-fiuoro-4-oxo-3,4-dihydropyrrolo[1,2-f][l,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With triethylamine In butan-1-ol for 2h; Reflux;62%
With triethylamine In butan-1-ol for 2h; Reflux;27 mg
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(3-hydroxymethyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester
475469-15-9

(3-hydroxymethyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester

[1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-hydroxymethyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester
1004991-84-7

[1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-hydroxymethyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 5h;60%
methanol
67-56-1

methanol

carbon monoxide
201230-82-2

carbon monoxide

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

C9H6N4O2
1095822-75-5

C9H6N4O2

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride at 100℃; under 5171.62 Torr; for 16h;58%
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-sulfamoylphenylboronic acid
613660-87-0

4-sulfamoylphenylboronic acid

4-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamide

4-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamide

Conditions
ConditionsYield
With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); tert-butylamine In water; isopropyl alcohol at 160℃; for 1h; Inert atmosphere;48%
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

1,2,3-tri-O-acetyl-5-O-benzoyl-5-(R)-C-methyl-β-D-ribofuranose
53872-91-6, 53872-94-9, 64761-44-0, 64761-45-1, 64761-46-2, 64761-47-3, 108836-00-6

1,2,3-tri-O-acetyl-5-O-benzoyl-5-(R)-C-methyl-β-D-ribofuranose

4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-5'(R)-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
141232-12-4

4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-5'(R)-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 24h; Heating;47%
piperidine
110-89-4

piperidine

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Stage #1: piperidine; 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile In tert-butyl alcohol for 2.5h; Heating / reflux;
Stage #2: With hydrogenchloride In diethyl ether; water; tert-butyl alcohol
Stage #3: With potassium hydroxide In water pH=7;
42%
In tert-butyl alcohol29 mg (42%)
(S)-7-fluoro-3-isobutyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride
1548341-44-1

(S)-7-fluoro-3-isobutyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-4-(2-(7-fluoro-3-isobutyl-4-oxo-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
1548335-67-6

(S)-4-(2-(7-fluoro-3-isobutyl-4-oxo-3,4-dihydropyrrolo[1,2-f][1,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
With triethylamine In butan-1-ol for 2h; Reflux;31%
With triethylamine In butan-1-ol for 2h; Reflux;31%
With triethylamine In butan-1-ol for 2h; Reflux;31%
1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose
60374-77-8, 80581-75-5, 89195-77-7, 115269-09-5, 115269-10-8

1,2,3-tri-O-acetyl-5-O-benzoyl-3-C-methyl-α-D-ribofuranose

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-3'-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
141232-11-3

4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-3'-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 24h; Heating;28%
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(1r,4r)-4-(dimethylamino)cyclohexan-1-ol

(1r,4r)-4-(dimethylamino)cyclohexan-1-ol

4-[[4-(dimethylamino)cyclohexyl]oxyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
1534374-53-2

4-[[4-(dimethylamino)cyclohexyl]oxyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions
ConditionsYield
Stage #1: (1r,4r)-4-(dimethylamino)cyclohexan-1-ol With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 0.5h;
Stage #2: 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile In tetrahydrofuran; mineral oil at 0℃; Reflux;
19%
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Vengicide
606-58-6

Vengicide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 31 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 53 percent / methanol. NH3 / 8 h / 110 °C
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-amino-5-cyano-7-(3'-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
141232-14-6

4-amino-5-cyano-7-(3'-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 28 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 51 percent / methanol. NH3 / 8 h / 110 °C
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

3'-C-methylsangivamycin
139209-27-1

3'-C-methylsangivamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 28 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 51 percent / methanol. NH3 / 8 h / 110 °C
3: 90 percent / 35percent aq. H2O2, conc. NH4OH / 1 h / Ambient temperature
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

5'(S)-C-methylsangivamycin
139209-29-3

5'(S)-C-methylsangivamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 32 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 55 percent / methanol. NH3 / 8 h / 110 °C
3: 100 percent / 35percent aq. H2O2, conc. NH4OH / 1 h / Ambient temperature
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

4-amino-5-cyano-7-(5'(S)-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine
141232-16-8

4-amino-5-cyano-7-(5'(S)-C-methyl-β-D-ribofuranosyl)pyrrolo<2,3-d>pyrimidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 32 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 55 percent / methanol. NH3 / 8 h / 110 °C
View Scheme
4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

sangivamycin
18417-89-5

sangivamycin

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 31 percent / 1,1,1,3,3,3-hexamethyldisilazane (HMDS), trimethylsilyl chloride (TMSCl), trimethylsilyl triflate (TMSOTf) / acetonitrile / 24 h / Heating
2: 53 percent / methanol. NH3 / 8 h / 110 °C
3: 87 percent / 35percent aq. H2O2, conc. NH4OH / 1 h / Ambient temperature
View Scheme
(R)-N-((3-aminopyrrolidin-3-yl)methyl)-2,4-difluorobenzamide

(R)-N-((3-aminopyrrolidin-3-yl)methyl)-2,4-difluorobenzamide

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-2,4-difluorobenzamide

(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-2,4-difluorobenzamide

Conditions
ConditionsYield
With sodium hydrogencarbonate for 10h; Reflux;
C12H16FN3O

C12H16FN3O

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
24391-41-1

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-4-fluorobenzamide

(S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-4-fluorobenzamide

Conditions
ConditionsYield
With sodium hydrogencarbonate for 10h; Reflux;

24391-41-1Relevant articles and documents

Preparation method 4 -chloro - 7H - pyrrolo [2, 3 - d] pyrimid -5 - carbonitrile

-

Paragraph 0035; 0042-0044; 0045; 0052-0054; 0055; 0061-0063, (2021/09/08)

The invention discloses a preparation method of 4 -chloro - 7H - pyrrolo [2, 3 - d] pyrimid -5 - carbonitrile which firstly utilizes phosphorus oxychloride and N, N - dimethyl formamide to prepare a vinol Michael reagent and 4 - chlorine - 7H - pyrrolo [2, 3 - d] pyrimidine to generate 4 -chloro - 7H - pyrrolo [2, 3 - d] pyrimidine -5 - formaldehyde. , 4 - Chloro - 7H - pyrrolo [2, 3 - d] pyrimidine -5 - formaldehyde is trioximated with hydroxylamine hydrochloride under the action of a base to obtain 4 -chloro - 7H - pyrrolo [2, 3 - d] pyrimidine -5 - formaldehyde oxime. The reaction of 4 - chloro - 7H - pyrrolo [2, 3 - d] pyrimid -5 - methanal oxime under the action of a dehydrating reagent generates 4 - chloro - 7H - pyrrolo [2, 3 - d] pyrimid -5 - carbonitrile. The raw materials adopted by the method are cheap and easily available, the synthesis method is simple to operate, the reaction conditions are mild, requirements on equipment are low, and the method is suitable for industrial large-scale production.

ASK1 INHIBITING PYRROLOPYRIMIDINE DERIVATIVES

-

Page/Page column 12; 44, (2012/06/30)

This invention relates to pyrrolopyrimidine derivatives of formula (I): where R1, X, p, R4, R2and R3are as defined herein, and their use as pharmaceuticals.

CHEMICAL COMPOUNDS, COMPOSITIONS AND METHODS FOR KINASE MODULATION

-

, (2011/12/04)

Chemical compounds that modulate kinase activity, including PI3 kinase activity, and chemical compounds, pharmaceutical compositions, and methods of treatment of diseases and conditions associated with kinase activity, including PI3 kinase activity, are described herein.

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