24391-41-1

Basic information

• Product Name: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
• Synonyms: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile;7H-Pyrrolo[2,3-d]pyriMidine-5-carbonitrile,4-chloro-;4-Chloro-7H-pyrrolo[2,3-d]pyrimidin-5-carbonitrile
• CAS NO: 24391-41-1
• Molecular Formula: C₇H₃ClN₄
• Molecular Weight: 178.582
• EINECS: 200-258-5
• Product Categories: intermediates;Heterocycle-Pyrimidine series
• Mol File: 24391-41-1.mol

Chemical Properties

• Boiling Point: 235.3±50.0 °C(Predicted)
• Appearance: /
• Density: 1.61 g/cm³
• Refractive Index: 1.708
• PKA: 8.84±0.20(Predicted)
• CAS DataBase Reference: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile(24391-41-1)
• EPA Substance Registry System: 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile(24391-41-1)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 24391-41-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile is used as a key intermediate in the synthesis of pharmaceutical compounds. Its unique structure and reactivity make it a valuable component in the development of new drugs, particularly those targeting various diseases and conditions.
Used in Agrochemical Research:
In the agrochemical industry, 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile is employed as a building block for the creation of novel agrochemicals. Its incorporation into these compounds can lead to the development of more effective pesticides, herbicides, and other agricultural products.
Used in Chemical Synthesis:
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile is used as a versatile reagent in the synthesis of complex organic molecules. Its presence in these molecules can impart unique properties and functionalities, making it an essential component in the creation of advanced materials and compounds for various applications.

InChI:InChI=1/C7H3ClN4/c8-6-5-4(1-9)2-10-7(5)12-3-11-6/h2-3H,(H,10,11,12)

Synthetic route

4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime (908287-23-0) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
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-carbonitrile (24391-41-1)

Conditions	Yield
With thionyl chloride In dichloromethane at 20 - 45℃;	89.4%

5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine (22276-95-5) + 4-tolyl thiocyanate (5285-74-5) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
With n-butyllithium In tetrahydrofuran; methanol; dichloromethane

4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (123148-78-7) + tri-n-butyltin cyanide (2179-92-2) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
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) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
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-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
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-carbonitrile (24391-41-1)

Conditions	Yield
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) + P-toluenesulfonyl cyanide (19158-51-1) → 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1)

Conditions	Yield
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) + benzyl spiro[indoline-3,4’-piperidine]-1‘-carboxylate (167484-18-6) → 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	Yield
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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → tert-butyl 2-(4-chloro-5-cyano-7H-pyrrolo[2,3-d]pyrimidin-7-yl)acetate

Conditions	Yield
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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (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)

Conditions	Yield
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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (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)

Conditions	Yield
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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (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)

Conditions	Yield
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) + (3-hydroxymethyl-pyrrolidin-3-yl)-carbamic acid tert-butyl ester (475469-15-9) → [1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-3-hydroxymethyl-pyrrolidin-3-yl]-carbamic acid tert-butyl ester (1004991-84-7)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 80℃; for 5h;	60%

methanol (67-56-1) + carbon monoxide (201230-82-2) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → C9H6N4O2 (1095822-75-5)

Conditions	Yield
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-sulfamoylphenylboronic acid (613660-87-0) → 4-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)benzenesulfonamide

Conditions	Yield
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) + 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) → 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)

Conditions	Yield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 24h; Heating;	47%

piperidine (110-89-4) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → 4-Piperidin-1-yl-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile

Conditions	Yield
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 alcohol	29 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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (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)

Conditions	Yield
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) + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → 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)

Conditions	Yield
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) + (1r,4r)-4-(dimethylamino)cyclohexan-1-ol → 4-[[4-(dimethylamino)cyclohexyl]oxyl]-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (1534374-53-2)

Conditions	Yield
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) → Vengicide (606-58-6)

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

Conditions	Yield
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) → 3'-C-methylsangivamycin (139209-27-1)

Conditions	Yield
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) → 5'(S)-C-methylsangivamycin (139209-29-3)

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

Conditions	Yield
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) → sangivamycin (18417-89-5)

Conditions	Yield
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 + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-2,4-difluorobenzamide

Conditions	Yield
With sodium hydrogencarbonate for 10h; Reflux;

C12H16FN3O + 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile (24391-41-1) → (S)-N-((3-amino-1-(5-cyano-7H-pyrrolo[2,3-d]pyrimidin-4-yl)pyrrolidin-3-yl)methyl)-4-fluorobenzamide

Conditions	Yield
With sodium hydrogencarbonate for 10h; Reflux;

Upstream product

• 22276-95-5 5-bromo-4-chloro-7H-pyrrolo[2,3-d]pyrimidine 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 3680-69-1 4-chloro-1H-pyrrolo[2,3-d]pyrimidine 
• 123148-78-7 4-chloro-5-iodo-7H-pyrrolo[2,3-d]pyrimidine 
• 2179-92-2 tri-n-butyltin cyanide 
• 5285-74-5 4-tolyl thiocyanate 
• 908287-23-0 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbaldehyde oxime 

Downstream Products

• 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 
• 141232-13-5 4-chloro-5-cyano-7-(2',3'-di-O-acetyl-5'-O-benzoyl-5'(S)-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 
• 606-58-6 Vengicide 
• 18417-89-5 sangivamycin 
• 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 
• 1548334-22-0 4-((2S,4S)-2-(5-chloro-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)-4-fluoropyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 1548332-62-2 (S)-4-(2-(5-chloro-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)azetidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 
• 1548332-49-5 (S)-4-(2-(5-chloro-4-oxo-3-phenyl-3,4-dihydropyrrolo[2,1-f][1,2,4]triazin-2-yl)pyrrolidin-1-yl)-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile 

Relevant articles and documents

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

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ASK1 INHIBITING PYRROLOPYRIMIDINE DERIVATIVES

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

HETEROCYCLIC COMPOUNDS AND USES THEREOF

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

CHEMICAL COMPOUNDS, COMPOSITIONS AND METHODS FOR KINASE MODULATION

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.

NEW ANTIVIRAL MODIFIED NUCLEOSIDES

This invention relates to novel compounds that have various medicinal applications, e.g. for the treatment and/or prevention of viral infections.

Heterocyclic Compounds Useful as RAF Kinase Inhibitors

The present invention provides compounds useful as inhibitors of Raf protein kinase. The present invention also provides compositions thereof, and methods of treating Raf-mediated diseases.

AMINE DERIVATIVES USEFUL AS ANTICANCER AGENTS

The invention relates to compounds of formula (I), or a pharmaceutically acceptable salt thereof, wherein: A is a moiety of formula (Il) and to pharmaceutically acceptable salts and solvates thereof, wherein X, Z, D, E, V, W, Y, R1, R2, R5, R6, L, and u are as defined herein. The invention also relates to methods of treating abnormal cell growth in mammals by administering the compounds of formula I to a patient in need thereof, and to compositions for treating such disorders which contain the compounds of formula (I). The invention also relates to methods of making the compounds of formula (I).

Monocyclic-7H-pyrrolo[2,3-d]pyrimidine compounds, compositions, and methods of use

Novel pyrrolo[2,3-d]pyrimidine compounds useful as inhibitors of the enzyme protein tyrosine kinases such as Janus Kinase 3 as well as immunosuppressive agents for organ transplants, lupus, multiple sclerosis, rheumatoid arthritis, psoriasis, Type I diabetes and complications from diabetes, cancer, asthma, atopic dermatitis, autoimmune thyroid disorders, ulcerative colitis, Crohn's disease, Alzheimer's disease, Leukemia and other autoimmune diseases are described.