Diisopropylethylamine → (R)-3-(2-((R)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one

Participants

Reaction Steps

A solution of (R)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one (97 mg, 0.35 mmol), 1-(biphenyl-4-yl)ethanamine hydrochloride (304 mg, 1.30 mmol, 3.7 equiv) and iPr2NEt (0.307 mL, 1.76 mmol, 5.0 equiv) in DMSO (1 mL) was heated at 110° C. for 1½ h and at 130° C. for 20 h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 10 to 50%) provided (R)-3-(2-((R)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one and (R)-3-(2-((S)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one.

Provenance & Evidence