2,5-Dichloropyrimidine → HCID 86664881, compound

Participants

Reaction Conditions

Reaction Steps

Palladium dichloro-bis(triphenylphosphine) (3.5 g) was added to a stirred solution of 4-formylbenzene boronic acid (32.5 g), 2,5-dichloro-pyrimidine (30 g) in toluene (1000 ml) and ethanol (100 ml) under an argon atmosphere. The solution was purged with argon and aqueous sodium carbonate (2N) (200 ml) was added. The reaction mixture was stirred at 60° C. for 90 minutes, cooled to ambient temperature, diluted with ethyl acetate, and washed successively with aqueous sodium hydrogen carbonate (saturated), water and brine. The combined organic extracts were treated with charcoal, dried over sodium sulfate, filtered through Hyflo® and concentrated in vacuo. The residue was triturated with diethyl ether (100 ml), the solid isolated by filtration and dried under high vacuum to give 4-(5-chloro-pyrimidin-2-yl)-benzaldehyde as a white solid. M.p. 186° C. 1H NMR (400 MHz, DMSO) 8.10 (d, 2H), 8.55 (d, 2H), 9.1 (s, 2H).

Provenance & Evidence