Phosphorus oxychloride → HCID 86647813, compound

Participants

Reaction Steps

A solution of 5-(4-fluorobenzyl)-2,6-dimethylpyrimidin-4-ol (730 mg, 3.14 mmol) in phosphorus oxychloride (10 mL) was stirred at 60° C. for 90 min. The reaction mixture was concentrated and ethyl acetate (50 mL) was added to the residue. The organic solution was washed with saturated sodium bicarbonate (50 mL), water (50 mL), and brine (50 mL), dried over sodium sulfate, filtered and concentrated. Column chromatography of the residue on silica (5-40% ethyl acetate in hexanes) afforded 4-chloro-5-(4-fluorobenzyl)-2,6-dimethylpyrimidine (527 mg, 67% yield) as a colorless solid. 1H NMR (400 MHz, CDCl3): 7.21 (m, 2H), 6.98 (m, 2H), 4.12 (s, 2H), 2.67 (s, 3H), 2.45 (s, 3H); MS (EI) for C13H12ClFN2: 250 (M+).

Provenance & Evidence