5-Bromopyrimidine-2-carbonitrile

143-33-9

32779-36-5

38275-57-9

General procedure for the synthesis of 5-bromo-2-cyanopyrimidine from sodium cyanide and 5-bromo-2-chloropyrimidine: 1. In a reaction flask, 5-bromo-2-chloropyrimidine (10 g, 51.8 mmol) was dissolved in dimethyl sulfoxide (26 mL). 2. a mixture of sodium cyanide (2.59 g, 51.8 mmol) and triethylenediamine (1.2 g, 10.4 mmol) in dimethyl sulfoxide (14 mL) and water (28 mL) was added sequentially to the above solution. 3. The reaction mixture was stirred at room temperature for 18 hours. 4. Upon completion of the reaction, the mixture was diluted with water (130 mL) and extracted with ether (3 x 150 mL). 5. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a light yellow solid. 6. The resulting solid was purified by recrystallization from hot dichloromethane to afford the target product 5-bromo-2-cyanopyrimidine. Yield: 99% (9.4 g). 1H NMR (CDCl3, 400 MHz) δ: 8.84 (s, 2H).