Isopropanol → 2-Cyclohexylmethyloxy-4-isopropoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750821Notes

Reaction equation

[CH:1]1([O:7][C:8]2[N:13]=[C:12](S(C)(=O)=O)[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][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:33]([Li])CCC.[CH:38]([OH:41])([CH3:40])[CH3:39]>>[CH:2]1([CH2:1][O:7][C:8]2[N:13]=[C:12]([O:41][CH:38]([CH3:40])[CH3:39])[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)[CH2:33][CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

Reactant 3

HCID 3776Isopropanol

HCID 69199838HCID 69199838, compound

HCID 178418339Butyllithium

Product 1

HCID 103239032-Cyclohexylmethyloxy-4-isopropoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

2-Cyclohexyloxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (HRf product, Example 51, Step A),(24 mg, 0.1 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-cyclohexylmethyloxy-4-isopropoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine. HPLC/Rt=5.47 min. 1H-NMR 500 MHz (CDCl3): δ 0.8 (m, 1H), 1.1 (m, 2H), 1.20-1.35 (m, 3H), 1.37 (d, J=6 Hz, 6H), 1.7-1.8 (m, 3H), 1.90 (m, 2H). 4.20 (d, J=6 Hz, 1H), 5.50 (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-3461903be387498288ac8f0a7a464e37
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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