Cyclohexanemethanol → 2-(Cyclohexylmethoxy)-4-(methyl-sulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

HRID 750820Notes

Reaction equation

HRID 750820 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([CH2:41][OH:42])[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1>>[CH:35]1([CH2:41][O:42][C:5]2[N:6]=[C:7]([S:26]([CH3:29])(=[O:27])=[O:28])[C:8]([C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=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

4

Reactant 3

HCID 7507CyclohexanemethanolHCID 597538832,4-Bis(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidineHCID 178418339Butyllithium

Product 1

HCID 692000542-(Cyclohexylmethoxy)-4-(methyl-sulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Procedure

2,4-bis(Methylsulfonyl)-5-[4-chlorophenyl]-6-[2,4-dichlorophenyl]pyrimidine (Reference Example 5) (98 mg, 0.2 mmol) was reacted with 1 equivalent each of n-butyl lithium and cyclohexyl methanol by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel eluted with 85/15 hexanes/ethyl acetate afforded 2-(cyclohexylmethoxy)-4-(methyl-sulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (HRf product): 1H-NMR 500 MHz (CDCl3): δ 0.9-1.1 (m, 1H), 1.10-1.2 (m, 2H), 1.2-1.4 (m, 3H); 1.67-1.88 (m, 3H), 1.9-2.0 (m, 2H), 3.38 (s, 3H), 4.29 (d, J=6 Hz, 2H), 7.0 (d, J=7 Hz, 1H), 7.18-7.22 (m, 3H), 7.24-7.28 (m, 2H), 7.36 (d, J=2 Hz, 1H) and 28 mg of 2-(methylsulfonyl)-4-(cyclohexylmethyloxy)-5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)pyrimidine (LRf 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), 7.08-7.12 (m, 2H), 7.22-7.30 (m, 4H), 7.36 (d, J=2 Hz, 1H).

Workup

  1. washWorkup and flash column chromatography on silica gel eluted with 85/15 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-61b03d6bde564feeace499570f3bf533
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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