Ammonia → (4s)-3-{4-[6-Amino-5-(Pyrimidin-2-Yl)pyridin-3-Yl]phenyl}-5,5-Dimethyl-4-Phenyl-1,3-Oxazolidin-2-One

Participants

Reaction Conditions

Reaction Steps

A 2-mL glass microwave reaction vessel was charged with ammonia (2 M solution in 2-propanol) (123 μL, 5.68 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) and (S)-3-(4-(6-fluoro-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (25 mg, 0.057 mmol) in DMSO (568 μL). The reaction mixture was stirred and heated at 100° C. in a heating block overnight. LC-MS indicated clean and complete conversion to the desired product. The material thus obtained was purified by reverse-phase preparative HPLC using 0.1% TFA in ACN/H2O, gradient 15% to 90% over 20 minutes to provide (S)-3-(4-(6-amino-5-(pyrimidin-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one as a yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 8.93 (d, J=5.02 Hz, 2H), 8.84 (d, J=2.46 Hz, 1H), 8.42 (d, J=2.56 Hz, 1H), 7.56 (s, 4H), 7.43 (t, J=4.81 Hz, 1H), 7.34-7.41 (m, 2H), 7.25-7.34 (m, 3H), 5.48 (s, 1H), 1.65 (s, 3H), 0.91 (s, 3H). m/z (ESI) 438.2 (M+H)+.

Provenance & Evidence