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

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Reaction Steps

Utilizing the general procedure outlined for 6-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one, 6-chloro-4-hydroxy-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one (374 mg, 1.1 mmol) was reacted with 1.0M allyl magnesium bromide (6.4 ml, 6.4 mmol) to afford 4-allyl-6-chloro-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one as a colorless oil. 1H NMR (CDCl3, 400 MHz) δ 9.88 (s, 1H), 7.29 (dd, J=2.4 and 8.6 Hz, 1H), 7.17 (s, 1H), 6.80 (d, J=8.8 Hz, 1H), 5.53 (m, 1H), 5.22 (m, 2H), 4.56 (m, 1H), 4.12 (m, 1H), 3.11 (m, 2H). MS (Electrospray): m/z 373.0 (M+).

Provenance & Evidence