3,4-Difluorobenzyl alcohol → HCID 59753928, compound

Participants

Reaction Steps

2-(Methylsulfonyl)-4-(cyclohexyloxy)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (LRf product) (Example 52, Step A), (24 mg, 0.045 mmol) was reacted with 1 equivalent each of n-butyl lithium and 3,4-difluorobenzyl alcohol by the procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 93/7 hexanes/ethyl acetate) afforded the title compound. HPLC/MS: m/e=577 (M++1); Rt=5.34 min; 1H-NMR 500 MHz (CDCl3): 1.28-1.40 (m, 3H), 1.40-1.55 (m, 2M), 1.50-1.60 (m, 2H), 1.60-1.70 (m, 2H), 1.8-1.90 (m, 2H), 5.26 (m, J=4 Hz, 1H), 5.40 (s, 2H), 7.03 (d, J=8 Hz, 2H), 7.05 (d, J=1 Hz), 7.15-7.27 (m, 5H), 7.34 (d over multiplet, J=2 Hz, 2H).

Provenance & Evidence