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

HRID 1850224Notes

Reaction equation

Cl[C:2]1[N:7]=[C:6]([N:8]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][O:10][C:9]2=[O:19])[CH:5]=[CH:4][N:3]=1.[CH:20]1([C@@H:23]([NH2:25])[CH3:24])[CH2:22][CH2:21]1>CN1C(=O)CCC1>[CH:20]1([C@@H:23]([NH:25][C:2]2[N:7]=[C:6]([N:8]3[C@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][O:10][C:9]3=[O:19])[CH:5]=[CH:4][N:3]=2)[CH3:24])[CH2:22][CH2:21]1

Participants

Conditions

Temperature: 180 °C

Procedure

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.

Workup

filtrationThe reaction mixture was filtered
custompurified by reverse phase HPLC

Sources & evidence

ORD record: ord-917e0112078b406894063be315b1cc73
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957068B2

Reaction notes

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