3,4-Difluorophenol → 2-(3,4-Difluorophenoxy)-4-cyclohexyloxy-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine

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Reaction Steps

2-(Methylsulfonyl)-4-(cyclohexyloxy)-5-(4-chlorophenyl)-6-(2,4-dichloro-phenyl)pyrimidine (Lower Rf product) (Example 52, Step A), (26 mg, 0.05 mmol) was reacted with 1 equivalent each of n-butyl lithium and 3,4-difluorophenol 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 title compound. HPLC/MS: m/e=563 (M++1); Rt=5.25 min. 1H-NMR 500 MHz (CDCl3): 1.28-1.40 (m, 4H), 1.55 (m, 3H), 1.65 (m, 2H), 1.90 (m, 2H), 5.03 (m, J=4 Hz, 1H), 7.05 (m, 4H), 7.10 (m, 5H), 7.34 (d, J=2 Hz, 1H).

Provenance & Evidence