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

Name
4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
EINECS 200-258-5
CAS No. 24391-41-1
Article Data12
CAS DataBase
Density 1.61 g/cm³
Solubility
Melting Point
Formula C₇H₃ClN₄
Boiling Point 235.3±50.0 °C(Predicted)
Molecular Weight 178.581
Flash Point
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile,4-chloro- (9CI);
PSA 65.36000
LogP 1.48298

Synthetic route

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

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

Conditions

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

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

Conditions

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

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

: 5285-74-5
4-tolyl thiocyanate

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

Conditions

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

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

: 2179-92-2
tri-n-butyltin cyanide

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

Conditions

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;

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

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

Conditions

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

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

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

Conditions

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

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

Conditions

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

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

: 19158-51-1
P-toluenesulfonyl cyanide

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

Conditions

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℃;

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

: 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

Conditions

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℃;

: 5292-43-3
bromoacetic acid tert-butyl ester

: 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

Conditions

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%

: 1548339-56-5
(S)-3-phenyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

: 24391-41-1
4-chloro-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

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;

: 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

: 24391-41-1
4-chloro-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

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%

: 1548341-37-2
(5)-7-fluoro-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

: 24391-41-1
4-chloro-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

Conditions	Yield
With triethylamine In butan-1-ol for 2h; Reflux;	62%
With triethylamine In butan-1-ol for 2h; Reflux;	27 mg

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

: 475469-15-9
(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

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

: 67-56-1
methanol

: 201230-82-2
carbon monoxide

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

: 1095822-75-5
C9H6N4O2

Conditions

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%

...Expand

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

: 613660-87-0
4-sulfamoylphenylboronic acid

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

Conditions

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%

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

: 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

: 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

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

: 110-89-4
piperidine

: 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

Conditions

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%)

: 1548341-44-1
(S)-7-fluoro-3-isobutyl-2-(pyrrolidin-2-yl)pyrrolo[1,2-f][1,2,4]triazin-4(3H)-one hydrochloride

: 24391-41-1
4-chloro-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

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%

: 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

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

: 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

Conditions	Yield
With chloro-trimethyl-silane; trimethylsilyl trifluoromethanesulfonate; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile for 24h; Heating;	28%

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

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

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

Conditions

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%

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

: 606-58-6
Vengicide

Conditions

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

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

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

Conditions

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

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

: 139209-27-1
3'-C-methylsangivamycin

Conditions

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

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

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

Conditions

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

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

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

Conditions

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

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

: 18417-89-5
sangivamycin

Conditions

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

: 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

Conditions

Conditions	Yield
With sodium hydrogencarbonate for 10h; Reflux;

: C12H16FN3O

: 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

Conditions

Conditions	Yield
With sodium hydrogencarbonate for 10h; Reflux;

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

The 7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile,4-chloro-, with the CAS registry number 24391-41-1, is also known as 4-Chloro-1H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile. This chemical's molecular formula is C₇H₃ClN₄ and molecular weight is 178.58. What's more, its IUPAC name is called 4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile.

Physical properties about 7H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile,4-chloro- are: (1)ACD/LogP: 1.202; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.20; (4)ACD/LogD (pH 7.4): 1.19; (5)ACD/BCF (pH 5.5): 4.83; (6)ACD/BCF (pH 7.4): 4.64; (7)ACD/KOC (pH 5.5): 107.36; (8)ACD/KOC (pH 7.4): 103.20; (9)#H bond acceptors: 4; (10)#H bond donors: 1; (11)#Freely Rotating Bonds: 0; (12)Polar Surface Area: 65.36 Å²; (13)Index of Refraction: 1.708; (14)Molar Refractivity: 43.227 cm³; (15)Molar Volume: 110.885 cm³; (16)Polarizability: 17.136×10^-24cm³; (17)Surface Tension: 96.477 dyne/cm; (18)Density: 1.61 g/cm³.

You can still convert the following datas into molecular structure:
(1) SMILES: Clc2ncnc1ncc(C#N)c12
(2) InChI: InChI=1S/C7H3ClN4/c8-6-5-4(1-9)2-10-7(5)12-3-11-6/h2-3H,(H,10,11,12)
(3) InChIKey: NEWCOPCSNFUQQY-UHFFFAOYSA-N

Product Name

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

Synthetic route

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

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