6-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one → 6-chloro-4-cyclopropyl-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 (217 mg, 0.62 mmol) was reacted with 0.5 M cyclopropyl magnesium bromide (4.9 ml, 2.5 mmol) to afford 6-chloro-4-cyclopropyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one as an oil. 1H NMR (CD3OD, 400 MHz) δ 7.89 (d, J=2.0 Hz, 1H), 7.36 (dd, J=2.4 and 8.6 Hz), 1H), 6.91 (dd, J=1.6 Hz and 7.6 Hz, 1H), 4.74 (m, 1H), 4.52 (m, 1H), 1.50 (m, 1H), 1.26 (m, 2H), 1.15 (m, 1H), 1.02 (m, 1H). Exact Mass (Electrospray, M+H) Calc'd, 373.0537; Found, 373.0541.

Provenance & Evidence