6-Bromoimidazo[1,2-a]pyrimidine-3-carbaldehyde

7752-82-1

2065-75-0

865156-67-8

General procedure for the synthesis of 6-bromoimidazo[1,2-A]pyrimidine-3-carbaldehyde from 2-amino-5-bromopyrimidine and 2-bromomalonaldehyde: 2-bromomalonaldehyde (500 mg, 2.90 mmol) was added to a solution of 2-amino-5-bromopyrimidine (526 mg, 3.49 mmol) in acetonitrile (20 mL). The reaction mixture was heated to reflux for 2 hours. Upon completion of the reaction, the reaction was quenched with saturated sodium bicarbonate solution (20 mL) and extracted with ethyl acetate (3 × 20 mL). The organic layers were combined, washed with saturated brine (20 mL) and dried over anhydrous sodium sulfate. The organic layers were concentrated under reduced pressure, and the resulting crude product was purified by silica gel column chromatography with gradient elution using chloroform/methanol (98:2 to 100:0, v/v) as eluent to afford the target product 6-bromoimidazo[1,2-A]pyrimidine-3-carbaldehyde. Yield: 40%; 1H NMR (DMSO-d6, 300 MHz): δ 9.98 (s, 1H), 9.75-9.76 (d, 1H, J = 2.4 Hz), 8.97-8.98 (d, 1H, J = 2.4 Hz), 8.70 (s, 1H); MS (m/z): 226 [M + H]+.