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

Participants

Reaction Steps

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).

Provenance & Evidence