2-Aminopyrimidine → 2-Methyl-3-[4-(trifluoromethyl)phenyl]imidazo[1,2-a]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Add 2-bromo-1-(4-(trifluoromethyl)phenyl)propan-1-one (100 g, 0.356 mol), 2-aminopyrimidine (33.85 g, 0.356 mol), and sodium bicarbonate (59.8 g, 0.811 mol) to toluene (500 mL) at 25 to 30° C. Heat the mixture to 90 to 100° C. and stir for 24 hours. Thereafter cool the mixture to 40 to 45° C., and distill the title compound under reduced pressure. Cool the distillate to 25 to 30° C.; add water (1 L); and stir the mixture 4 hours. Filter the mixture collecting the solid, and then wash the solid with a 10% solution of MTBE (200 mL) in hexane. Dry the solid under vacuum at 45 to 50° C. for 12 hours to give the title compound (35.4 g, 35% yield). 1H NMR (300 MHz, CDCl3) δ 8.58 (q, 1H), 8.24-8.26 (d, J=6.6 Hz, 1H), 8.00-8.02 (d, J=8.1 Hz, 2H), 7.72-7.75 (d, J=8.4 Hz, 2H), 6.92-6.96 dd, J=3.9 Hz and 4.2 Hz, 1H), 2.69 (s, 3H).

Provenance & Evidence