2-Bromopropanedial → 6-Bromoimidazo[1,2-a]pyrimidine-3-carbaldehyde
Reaction equation
Br[CH:2]([CH:5]=[O:6])[CH:3]=O.[Br:7][C:8]1[CH:9]=[N:10][C:11]([NH2:14])=[N:12][CH:13]=1>C(#N)C>[Br:7][C:8]1[CH:9]=[N:10][C:11]2[N:12]([C:2]([CH:5]=[O:6])=[CH:3][N:14]=2)[CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Bromomalonaldehyde (500 mg, 2.90 mmol) was added to a solution of 5-bromopyrimidin-2-amine (526 mg, 3.49 mmol) in acetonitrile. The reaction mixture was refluxed for 2 hours. After completion of the reaction, the reaction mixture was quenched with sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was washed with brine and dried over sodium sulfate. The organic layer was concentrated and the product was purified by column chromatography using up to 2% methanol in chloroform gradient to obtain the title compound. 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, 2.4 Hz), 8.70 (s, 1H); MS (m/z): 226 (M+1)+.