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

Participants

Reaction Steps

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).

Provenance & Evidence