Cyclohexanol → HCID 69199838, compound

HRID 750822Notes

Reaction equation

CS([C:5]1[N:10]=[C:9]([C:11]2[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=2[Cl:18])[C:8]([C:19]2[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=2)=[C:7]([S:26]([CH3:29])(=[O:28])=[O:27])[N:6]=1)(=O)=O.C([Li])CCC.[CH:35]1([OH:41])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH:35]1([O:41][C:5]2[N:6]=[C:7]([S:26]([CH3:29])(=[O:28])=[O:27])[C:8]([C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)=[C:9]([C:11]3[CH:16]=[CH:15][C:14]([Cl:17])=[CH:13][C:12]=3[Cl:18])[N:10]=2)[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1

Participants

Reactant 3

HCID 7966Cyclohexanol

HCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HCID 178418339Butyllithium

Product 1

HCID 69199838HCID 69199838, compound

Procedure

2,4-Bis(methylsulfonyl)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 5) (196 mg, 0.4 mmol) was reacted with 1 equivalent each of n-butyl lithium and cyclohexanol by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 90/10 hexanes/ethyl acetate) afforded 2-cyclohexyloxy-4-(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Higher Rf product): 1H-NMR 500 MHz (CDCl3): δ 1.30 (m, 5H), 1.45 (m, 1H), 1.55 (m, 1H), 1.64 (m, 1H), 1.75 (m, 1H), 1.90 (m, 1H), 2.15 (m, 1H), 3.38 (s, 3H), 5.09 (m, 1H), 7.0 (d, J=7 Hz, 1H), 7.18-7.22 (m, 4H), 7.36 (d over m, J=2 Hz, 2H); and 2-methylsulfonyl-4-cyclohexyl-oxy-5-(4chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Lower Rf product): 1H-NMR 500 MHz (CDCl3): δ 0.87-0.9 (m, 1H), 0.95-1.07 (m, 2H), 1.1-1.3 (m, 2H), 1.33 (m, 2H), 1.7-1.82 (m, 4H), 3.40 (s, 3H), 4.37 (d, J=6 Hz, 2H), 7.08 (d, J=8 Hz, 2H), 7.12 (d, J=8 Hz, 1H), 7.22-7.30 (m, 3H), 7.37 (d, J=2 Hz, 1H).

Sources & evidence

ORD record: ord-c3928689330b45c9ac06cf8979c637c8
Source dataset: uspto-grants-2008_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07405221B2

Reaction notes

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