Water → HCID 86730138, compound

Participants

Reaction Steps

To a solution of 2,4-dichloropyrimidine (46.5 mg, 0.312 mmol) and (S)-4-(biphenyl-4-yl)oxazolidin-2-one (74.7 mg, 0.312 mmol) in DMF (700 μL) was added NaH (60% wt., 10.49 mg, 0.437 mmol) in two portions within ˜5 min [Caution: exotherm; gas development] at room temperature (water bath). The reaction mixture was stirred for 1.5 hour. The mixture was diluted with EtOAc (25 mL), stirred for 5 min and then diluted slowly with diluted brine (10 mL; 1:1 brine/water). The mixture was poured into diluted brine (40 mL) and EtOAc (25 mL). The separated organic phase was washed with diluted brine (3×40 ml), dried over Na2SO4, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane] to provide (S)-4-(biphenyl-4-yl)-3-(2-chloropyrimidin-4-yl)oxazolidin-2-one (49.5 mg). LCMS m/z 352.2 (M+H)+, Rt 1.06 min.

Provenance & Evidence