(S)-1-Cyclopropylethylamine → (R)-3-(2-(((S)-1-cyclopropylethyl)amino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one (55.3 mg, 0.20 mmol), (S)-1-cyclopropylethylamine (40 μL, 0.26 mmol, 1.3 equiv) and iPr2Net (0.20 mL, 1.15 mmol, 5.7 equiv) in NMP (1 mL) was heated in the microwave at 180° C. for 20 min. The reaction mixture was filtered and purified by reverse phase HPLC to give (R)-3-(2-(((S)-1-cyclopropylethyl)amino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one as a white solid (8.8 mg) in 10% yield. 1H NMR (400 MHz, CD3OD) δ 7.72 (d, J=6.26 Hz, 1H), 7.29-7.43 (m, 6H), 5.76 (dd, J=4.11, 8.80 Hz, 1H), 4.28 (dd, J=4.30, 8.61 Hz, 1H), 3.06-3.19 (m, 1H), 1.39 (dd, J=3.52, 6.65 Hz, 1H), 0.88-0.97 (m, 1H), 0.83 (br. s., 3H), 0.53-0.62 (m, 1H), 0.50 (dt, J=4.11, 8.51 Hz, 1H), 0.33 (qd, J=4.78, 9.54 Hz, 1H), 0.26 (td, J=4.60, 9.59 Hz, 1H); HRMS(A) m/z 325.1667 (M+H)+, Rt 1.54 min; UPLC 2.807 min.

Provenance & Evidence