Ammonia → (4s)-3-{4-[6-Amino-5-(Pyrimidin-2-Yl)pyridin-3-Yl]phenyl}-5,5-Dimethyl-4-Phenyl-1,3-Oxazolidin-2-One
Reaction equation
[NH3:1].F[C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C@@H:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]([CH3:27])([CH3:26])[O:17][C:16]3=[O:28])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1>CS(C)=O>[NH2:1][C:3]1[N:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([N:15]3[C@@H:19]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)[C:18]([CH3:27])([CH3:26])[O:17][C:16]3=[O:28])=[CH:11][CH:10]=2)=[CH:5][C:4]=1[C:29]1[N:34]=[CH:33][CH:32]=[CH:31][N:30]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
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)+.
Sources & evidence
- ORD record
- ord-52f1e46123494b4b90f7cb22a3aae3f0
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340549B2
Reaction notes
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