4-allyl-6-chloro-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one → 6-chloro-4-propyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one

Participants

Reaction Steps

A mixture of 4-allyl-6-chloro-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (42 mg, 0.11 mmol), ethyl acetate (3.5 ml) and 10% Pd/C (10 mg) was placed under hydrogen atmosphere (1 atm) at room temperature and stirred overnight. After bubbling nitrogen through reaction mixture, the mixture was filtered through a Celite, washing with ethyl acetate. The collected filtrate was concentrated to give an oil which was purified by reverse phase prep HPLC to afford 6-chloro-4-propyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one as a white solid. 1H NMR (CD3OD, 400 MHz) δ 7.40 (s, 1H), 7.35 (dd, J=2.4 and 8.6 Hz, 1H), 6.86 (d, J=8.8 Hz 1H), 4.45 (m, 1H), 4.27 (m, 1H), 2.47 (m, 1H), 2.17 (m, 1H), 1.23 (m, 2H), 0.96 (t, J=7.2 Hz, 3H).

Provenance & Evidence