Potassium Phosphate, Tribasic → 2-chloro-4-cyclopropyl-5-fluoroPyrimidine

Participants

Reaction Conditions

Reaction Steps

5-Fluoro-2,4-dichloropyrimidine (5 g, 29.9 mmol), cyclopropyl boronic acid (2.57 g, 29.9 mmol), potassium phosphate tribasic (15.89 g, 74.9 mmol) and PdCl2(dppf)-dichloromethane adduct (1.223 g, 1.497 mmol) were added to a dry flask. The system was degassed with argon, and then tetrahydrofuran (150 mL) was added. The reaction mixture was degassed with argon for five minutes, and then heated to 67° C. After 12 hours, the reaction mixture was diluted with ethyl acetate (1000 mL), washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in hexanes to afford 2-chloro-4-cyclopropyl-5-fluoropyrimidine (4.1 g, 23.8 mmol, 79% yield). MS ESI: [M+H]+ m/z 172.9.

Provenance & Evidence