CAS No.24391-41-1,4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile Suppliers

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Basic Information

Molecular Structure:
CAS No.:	24391-41-1
Name:	4-Chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carbonitrile
Article Data:	12

Formula:	C₇H₃ClN₄
Molecular Weight:	178.581
Synonyms:	1H-Pyrrolo[2,3-d]pyrimidine-5-carbonitrile,4-chloro- (9CI);
EINECS:	200-258-5
Density:	1.61 g/cm³
Boiling Point:	235.3±50.0 °C(Predicted)
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%

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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