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
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=[CH:24][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=C>>[CH2:22]([C:5]1([C:18]([F:20])([F:21])[F:19])[C:4]2[C:9](=[CH:10][CH:11]=[C:2]([Cl:1])[CH:3]=2)[NH:8][C:7](=[O:12])[N:6]1[CH2:13][C:14]([F:15])([F:17])[F:16])[CH:23]=[CH2:24]Participants
4
Reactant 3
Product 1
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 (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+).
Sources & evidence
- ORD record
- ord-02f9009bab2c4df1afcbd6f361077aba
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07745452B2
Reaction notes
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