Isopropanol → 2-Isopropoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

Participants

Reaction Steps

2-Cyclohexyloxy-4-(methylsulfonyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Higher Rf product) (Example 52, Step A), (26 mg, 0.05 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-isopropoxy-4-methylsulfonyl-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine and 2-cyclohexyloxy)-4-isopropoxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (HRf product): HPLC/MS: m/e=493 (M++1); Rt=5.26 min. 1H-NMR 500 MHz (CDCl3): δ 0.9 (m, 1H), 1.30 (m, 1H), 1.35) d, J=6 Hz, 6H), 1.42 (m, 2H), 1.65 (m, 3H), 1.90 (m, 2H), 2.15 (m, 2H), 5.03 (m, J=4 Hz, 1H), 5.47 (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