Dichloromethane → 5-Bromopyrimidine-2-carbonitrile

A solution of 5-bromo-2-chloropyrimidine (10 g, 51.8 mmol) in dimethylsulfoxide (26 mL) was added to a mixture of sodium cyanide (2.59 g, 51.8 mmol) and triethylenediamine (1.2 g, 10.4 mmol) in dimethylsulfoxide (14 mL) and water (28 mL). The resulting mixture was stirred for 18 hours at room temperature. The mixture was then diluted with water (130 mL) and extracted with diethyl ether (3×150 mL). 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, 9.4 g.

1. extractionextracted with diethyl ether (3×150 mL)
2. dry with materialThe combined organic solutions were dried over sodium sulfate
3. concentrationconcentrated in vacuo
4. customto give a pale yellow solid

ORD record

ord-9219790b8ce84a36b89729a2ed34a894

Source dataset

uspto-grants-2011_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07875615B2