Water → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of (S)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one (40 mg, 0.145 mmol), 1,1,1-trifluoropropan-2-amine (82 mg, 0.725 mmol), Hunig's Base (0.038 mL, 0.218 mmol) in DMSO (0.4 mL) was heated under argon at 115° C. for ˜3 days. Then mixture was allowed to cool to room temperature. The mixture was diluted with DMSO and water (˜10 vol. % of DMSO), filtered through a syringe filter and purified by reverse phase HPLC. Selected fractions were collected and lyophilized providing (45)-4-phenyl-3-(2-(1,1,1-trifluoropropan-2-ylamino)pyrimidin-4-yl)oxazolidin-2-one (ratio of two isomers: 7/3) as white solid as its trifluoroacetic acid salt. LCMS m/z 353.2 (M+H)+, Rt 0.78 min. HRMS(A) m/z 353.1231 (M+H)+, Rt 1.92/1.96 min.

Provenance & Evidence