ChemicalBook CAS DataBase List 5-Bromopyrimidine-2-carbonitrile

5-Bromopyrimidine-2-carbonitrile synthesis

3synthesis methods

Product Name:5-Bromopyrimidine-2-carbonitrile
CAS Number:38275-57-9
Molecular formula:C5H2BrN3
Molecular Weight:183.99

5-Bromopyrimidine-2-carbonitrile is a pharmaceutical intermediate that can be obtained by reacting 5-bromo-2-chloropyrimidine with potassium nitride. It can also be obtained as follow: 5-Bromo-2-chloropyrimidine (7.51 g, 38.83 mmol), dissolved in DMSO (20 mL), is added to a mixture of NaCN (1.9 g, 38.83 mmol) and l,4-diazabicyclo[2,2,2]octane (0.87 g, 7.77 mmol) in DMSO (10 mL) and water (20 mL). The mixture is stirred overnight, and then water (100 mL) is added. The mixture is extracted with ether (3x100 mL). The combined organic layer is dried (Na2SO4), filtered, and concentrated in vacuo to afford 5-Bromopyrimidine-2-carbonitrile as a solid.

143-33-9 Synthesis

143-33-9
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32779-36-5 Synthesis

32779-36-5
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$5.00/5g

38275-57-9
201 suppliers
$5.00/1g

Yield:38275-57-9 99%

Reaction Conditions:

with 1,4-diaza-bicyclo[2.2.2]octane in water;dimethyl sulfoxide at 20; for 18 h;

Steps:

63
Preparation 63 5-Bromo-pyrimidine-2-carbonitrile A solution of 5-bromo-2-chloropyrimidine (10g, 51.8mmol) in dimethylsulfoxide (26ML)-WAS-ADDED TO : A MIXTURE, of sodium cyandie (2.59g, 51.8mmol) and triethylenediamine (1. 2g, 10. 4mmol) in dimethylsulfoxide (14mL) and water (28ML). THE RESULTING mixture was stirred for 18 hours at ROOM TEMPERATURE. THE ; mixture was-then diluted with water (130MOLY and extracted with diethyl ether (3x150mL) the combined organic solutions were dried over sodium sulfate and concentrated in vacuo to give a pale yellow solid. Re-crystallisation of the solid from hot dichloromethane afforded the title product in 99% yield, 9.4g. 1HNMR (CDCL3, 400MHZ) No.: 8.84 (S, 2H).

References:

PFIZER LIMITED;PFIZER INC. WO2005/28452, 2005, A1 Location in patent:Page/Page column 87

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773837-37-9 Synthesis