Isopropanol → 2-Isopropoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine
Reaction equation
[CH:1]1([O:7][C:8]2[N:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[C:11]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=3)=[C:10]([C:25]3[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=3[Cl:32])[N:9]=2)[CH2:6]CCC[CH2:2]1.C([Li])CCC.[CH:38]([OH:41])([CH3:40])[CH3:39]>>[CH:1]([O:7][C:8]1[N:13]=[C:12]([S:14]([CH3:17])(=[O:16])=[O:15])[C:11]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[C:10]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:9]=1)([CH3:6])[CH3:2].[CH:38]([O:41][C:12]1[C:11]([C:18]2[CH:19]=[CH:20][C:21]([Cl:24])=[CH:22][CH:23]=2)=[C:10]([C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[CH:27][C:26]=2[Cl:32])[N:9]=[CH:8][N:13]=1)([CH3:40])[CH3:39]Participants
Procedure
2-Cyclohexyloxy-4-(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Higher Rf product) (Example 52, Step A), (26 mg, 0.05 mmol) was reacted with 1 equivalent each of n-butyl lithium and isopropanol by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 95/5 hexanes/ethyl acetate) afforded 2-isopropoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine and 2-cyclohexyloxy)-4-isopropoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (HRf product): HPLC/MS: m/e=493 (M++1); Rt=5.26 min. 1H-NMR 500 MHz (CDCl3): δ 0.9 (m, 1H), 1.30 (m, 1H), 1.35) d, J=6 Hz, 6H), 1.42 (m, 2H), 1.65 (m, 3H), 1.90 (m, 2H), 2.15 (m, 2H), 5.03 (m, J=4 Hz, 1H), 5.47 (qn, J=6 Hz, 1H), 7.03 (d, J=7 Hz, 1H), 7.10 (d, J=8 Hz, 1H), 7.18 (m, 4H), 7.32 (d, J=2 Hz, 1H).
Sources & evidence
- ORD record
- ord-b0a1905479e042f192965f1ba16d34c6
- Source dataset
- uspto-grants-2008_07
- Patent number
- US07405221B2
Reaction notes
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