HCID 10928782, compound → HCID 86746696, compound

Participants

Reaction Conditions

Reaction Steps

In a separate flask, a solution of 4-(4-fluorophenyl)-6-(1-methylethyl)-2-phenyl-5-(2,2-dibromovinyl)-pyrimidine obtained in step (v) above (1.000 gm, 2.10 mmol) in tetrahydrofuran (THF) (10 ml) was added dropwise to a -78° C. THF solution (15 ml) of n-butyl lithium (nBuLi) (2.5M in hexane, 1.68 ml, 4.20 mmol). The solution was allowed to stir 1 hour at -78° C., then cannulated into a THF solution (20 ml) of (S)-4-(methoxychlorophosphinyl)-3-[[(t-butyl)diphenylsilyl]-oxy]butanoic acid, methyl ester obtained in step (f) above which had also been cooled to -78° C. The resultant solution was stirred for 30 minutes, then quenched with saturated NH4Cl (15 ml) and warmed to 0° C. Then, saturated NaHCO3 was added to the solution which was subsequently warmed to room temperature. The mixture was diluted with ether and the organic layer was washed with brine, then dried over Na2SO 4, filtered and concentrated to give an orange oil. The oil was purified by flash chromatography on Merck silica gel in 30-50% EtOAc in hexane. The desired fractions were combined and evaporated to afford the title compound as yellow foam (0.732 gm, 49%). TLC: Rf =0.50 (50% EtOAc in hexane).

Provenance & Evidence