Sodium Carbonate → (S)-3-(4-(2-aminopyrimidin-5-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one
Reaction equation
I[C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:15][C:16]1([CH3:43])[O:20][C:19](=[O:21])[N:18]([C:22]2[CH:27]=[CH:26][C:25](B3OC(C)(C)C(C)(C)O3)=[CH:24][CH:23]=2)[C@H:17]1[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>O1CCOCC1>[NH2:8][C:5]1[N:4]=[CH:3][C:2]([C:25]2[CH:24]=[CH:23][C:22]([N:18]3[C@@H:17]([C:37]4[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=4)[C:16]([CH3:15])([CH3:43])[O:20][C:19]3=[O:21])=[CH:27][CH:26]=2)=[CH:7][N:6]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
5-Iodopyrimidin-2-amine (84 mg, 0.381 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.), sodium carbonate (2M, 254 μL, 0.509 mmol), (S)-5,5-dimethyl-4-phenyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazolidin-2-one (100 mg, 0.254 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium (II) (20.76 mg, 0.025 mmol, commercially available from Sigma-Aldrich, Milwaukee, Wis.) were combined in dioxane (848 μL) and stirred at 130° C. for 2 hours. LC-MS indicated complete conversion to the desired product. The reaction mixture was passed through a syringe filter, and 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-(2-aminopyrimidin-5-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one as a tan solid. 1H NMR (500 MHz, DMSO-d6) δ 8.50 (s, 2H), 7.53 (s, 4H), 7.34-7.41 (m, 2H), 7.22-7.33 (m, 3H), 6.70 (s, 2H), 5.47 (s, 1H), 1.64 (s, 3H), 0.91 (s, 3H). m/z (ESI) 361.2 (M+H)+.
Sources & evidence
- ORD record
- ord-edc8127324cb479ea76782fc0578f67d
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09340549B2
Reaction notes
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