N,N'-Dimethylethylenediamine → (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)pyridin-1 (2H)-yl)phenyl)-4-phenyloxazolidin-2-one

HRID 525406Notes

Reaction equation

HRID 525406 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:11]([CH3:20])([CH3:19])[O:10][C:9]2=[O:21])=[CH:4][CH:3]=1.[N:22]1[CH:27]=[CH:26][CH:25]=[N:24][C:23]=1[C:28]1[CH:29]=[CH:30][C:31](=[O:34])[NH:32][CH:33]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].CNCCNC>[Cu]I.O1CCOCC1>[CH3:19][C:11]1([CH3:20])[O:10][C:9](=[O:21])[N:8]([C:5]2[CH:6]=[CH:7][C:2]([N:32]3[CH:33]=[C:28]([C:23]4[N:22]=[CH:27][CH:26]=[CH:25][N:24]=4)[CH:29]=[CH:30][C:31]3=[O:34])=[CH:3][CH:4]=2)[C@H:12]1[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 4

HCID 8070N,N'-DimethylethylenediamineHCID 62657Potassium Phosphate, TribasicHCID 580164905-(pyrimidin-2-yl)pyridin-2(1H)-oneHCID 89813884(S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one2×

Product 1

HCID 89827444(S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)pyridin-1 (2H)-yl)phenyl)-4-phenyloxazolidin-2-oneYield 70.1%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
140 °C

Procedure

A microwave vial was charged with (S)-3-(4-iodophenyl)-5,5-dimethyl-4-phenyloxazolidin-2-one (Intermediate C)(0.100 g, 0.254 mmol), 5-(pyrimidin-2-yl)pyridin-2(1H)-one (0.048 g, 0.280 mmol), tribasic potassium phosphate (0.270 g, 1.272 mmol) and dioxane (2.5 mL). The mixture was purged with argon and then copper (I) iodide (0.048 g, 0.254 mmol) and N,N′-dimethylethylenediamine (0.055 mL, 0.509 mmol) were added. The system was purged with argon, the tube was sealed, and the reaction mixture was heated at 140° C. for 4 hours in the microwave. The reaction mixture was then filtered through Celite® brand filter aid and the filtrate was concentrated to afford a green solid. The resulting green solid was purified using column chromatography on silica gel (RediSep 40 g column, gradient elution with 50-100% EtOAc-hexane) to afford (S)-5,5-dimethyl-3-(4-(2-oxo-5-(pyrimidin-2-yl)pyridin-1 (2H)-yl)phenyl)-4-phenyloxazolidin-2-one (0.078 g, 0.178 mmol, 70% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 0.93 (s, 3H), 1.66 (s, 3H), 5.52 (s, 1H), 6.60 (dd, J=9.59, 0.59 Hz, 1H), 7.21-7.53 (m, 8H), 7.59-7.71 (m, 2H), 8.36 (dd, J=9.63, 2.59 Hz, 1H), 8.43-8.53 (m, 1H), 8.79 (d, J=4.89 Hz, 2H). m/z (ESI) 439 (M+H)+.

Workup

  1. customThe mixture was purged with argon
  2. customThe system was purged with argon
  3. customthe tube was sealed
  4. filtrationThe reaction mixture was then filtered through Celite® brand
  5. filtrationfilter aid
  6. concentrationthe filtrate was concentrated
  7. customto afford a green solid
  8. customThe resulting green solid was purified

Sources & evidence

ORD record
ord-68ac63ee315f4aeebd683f5a7b9a8b11
Source dataset
uspto-grants-2016_05
Patent number
US09340549B2

Reaction notes

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