Sodium Carbonate → HCID 89813784, compound

HRID 525399Notes

Reaction equation

HRID 525399 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[NH2:16][C:17]1[N:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([N:29]3[C@@H:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:32]([CH3:41])([CH3:40])[O:31][C:30]3=[O:42])=[CH:25][CH:24]=2)=[CH:19][C:18]=1B1OC(C)(C)C(C)(C)O1>O1CCOCC1>[NH2:16][C:17]1[C:18]([C:2]2[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=2)=[CH:19][C:20]([C:23]2[CH:24]=[CH:25][C:26]([N:29]3[C@@H:33]([C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)[C:32]([CH3:40])([CH3:41])[O:31][C:30]3=[O:42])=[CH:27][CH:28]=2)=[CH:21][N:22]=1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2466472-Chloropyrimidine-4-carbonitrileHCID 89815354HCID 89815354, compound

Product 1

HCID 89813784HCID 89813784, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

2-Chloropyrimidine-4-carbonitrile (22.42 mg, 0.161 mmol), Na2CO3 (134 μL, 0.268 mmol), (S)-3-(4-(6-amino-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl)phenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (65 mg, 0.134 mmol), and dichloro(1,1-bis(diphenylphosphinoferrocene))palladium(II) (10.94 mg, 0.013 mmol) were combined in dioxane (268 μL) and stirred at 100° C. in a microwave oven for 1 hour. LC-MS indicated good conversion to desired product. After cooling to room temperature, the reaction mixture was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 0% to 10% MeOH in DCM, to provide (S)-2-(2-amino-5-(4-(5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)phenyl)pyridin-3-yl)pyrimidine-4-carbonitrile as yellow solid. 1H NMR (500 MHz, DMSO-d6) δ 10.56 (s, 1H), 8.83 (d, J=4.70 Hz, 1H), 8.59 (d, J=2.67 Hz, 1H), 8.13 (d, J=8.44 Hz, 1H), 8.06 (dd, J=2.14, 6.30 Hz, 1H), 7.66 (d, J=8.66 Hz, 2H), 7.58 (d, J=8.87 Hz, 2H), 7.49 (d, J=4.49 Hz, 1H), 7.35-7.42 (m, 2H), 7.23-7.35 (m, 3H), 5.49 (s, 1H), 1.66 (s, 3H), 0.92 (s, 3H). m/z (ESI) 463.8 (M+H)+.

Sources & evidence

ORD record
ord-3d9babbc9fc14f74bf5015f39a0fa611
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

Loading…