Tripropylamine → 4-Chloro-6-methyl-2-(2-trifluoromethyl-phenyl)-pyrimidine

Participants

Reaction Conditions

Reaction Steps

A solution of 6-methyl-2-(2-trifluoromethyl-phenyl)-3H-pyrimidin-4-one (10.7 g, 41.9 mmol) in phosphorous oxychloride (39 mL, 419 mmol) was treated with tri-n-propylamine (16 mL, 83.9 mmol) and refluxed at 110-120° C. for 1 hours. The solvent was evaporated, azeotroped three times with toluene, then dried in vacuo. The residue was taken up in ethyl acetate, washed sequentially with 1 N sodium hydroxide, water and brine, then dried over sodium sulfate and concentrated. Purification by flash chromatography [SiO2, ethyl acetate:hexanes (1:9)] provided the title compound (9.61 g, 84% yield) as an orange oil. 1H NMR (CDCl3, 500 MHz) δ 2.63 (3H, s), 7.26 (s, 1H), 7.61 (t, J=7.6 Hz, 1H), 7.67 (t, J=7.5 Hz, 1H), 7.76 (d, J=7.6 Hz, 1H), 7.82 (d, J=7.8 Hz, 1H) ppm; MS (FIA) 273.0 (M+H); Rt (Method A) 3.499 min.

Provenance & Evidence