5-fluoropyriMidine-2-carbaldehyde

38275-55-7

935667-50-8

General procedure for the synthesis of 5-fluoropyrimidine-2-carbaldehyde from 2-cyano-5-fluoropyrimidine: To an anhydrous THF solution of 5-fluoropyrimidine-2-carbonitrile (1.0 g, 8.1 mmol) was slowly added a solution of DIBAL-H (8.1 mL) over a period of 20 min at -78 °C. The reaction mixture was continued to be stirred at this temperature for 2 h. The reaction was subsequently quenched by the addition of MeOH. The reaction system was slowly warmed to room temperature and then concentrated HCl solution was added. The resulting mixture was stirred at room temperature for 2 h before being extracted with an aqueous layer and EtOAc (3 times). The combined organic phases were washed with brine and dried over MgSO4. The solvent was removed by concentration under reduced pressure to give 5-fluoropyrimidine-2-carbaldehyde (780 mg, 76% yield). Mass spectrometry result: [M+H]+ 127.