6-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-one → 6-chloro-4-ethyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin2(1H)-one

HRID 19703Notes

Reaction equation

HRID 19703 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]2([C:22]1C=CC=C[CH:23]=1)[C:18]([F:21])([F:20])[F:19].ClC1C=C2C(=CC=1)NC(=O)N(CC(F)(F)F)C2(O)C(F)(F)F.C([Mg]Br)C>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[N:6]([CH2:13][C:14]([F:17])([F:16])[F:15])[C:5]2([CH2:22][CH3:23])[C:18]([F:20])([F:21])[F:19]

Participants

4

Reactant 3

HCID 118540726-chloro-4-phenyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin-2(1H)-oneHCID 593466016-Chloro-4-hydroxy-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydro-quinazolin-2(1H)-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 118540746-chloro-4-ethyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin2(1H)-one

Procedure

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 (227 mg, 0.65 mmol) was reacted with 3.0M ethyl magnesium bromide (0.9 ml, 2.6 mmol) to afford 6-chloro-4-ethyl-3-(2,2,2-trifluoroethyl)-4-(trifluoromethyl)-3,4-dihydroquinazolin2(1H)-one as a white solid. 1H NMR (d6-DMSO, 400 MHz) δ 7.41 (s, 1H), 7.35 (dd, J=2.4 and 8.6 Hz, 1H), 6.88 (d, J=8.8 Hz, 1H), 4.52 (m, 1H), 4.26 (m, 1H), 2.55 (m, 1H), 2.36 (m, 1H), 0.9 (t, J=6.8 Hz, 3H). Exact Mass (Electrospray, M+H) Calc'd, 361.0537; Found, 361.0532.

Sources & evidence

ORD record
ord-4212fc3454be402f8e59e3d3b916f038
Source dataset
uspto-grants-2010_06
Patent number
US07745452B2

Reaction notes

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