Sodium hydride → 3-(2-Chloropyrimidin-4-yl)-4-(2-fluoropropan-2-yl)oxazolidin-2-one

HRID 57372Notes

Reaction equation

HRID 57372 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[F:9][C:10]([CH:13]1[CH2:17][O:16][C:15](=[O:18])[NH:14]1)([CH3:12])[CH3:11].[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:1][C:2]1[N:7]=[C:6]([N:14]2[CH:13]([C:10]([F:9])([CH3:12])[CH3:11])[CH2:17][O:16][C:15]2=[O:18])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 904144754-(2-Fluoropropan-2-yl)oxazolidin-2-one

Product 1

HCID 904147503-(2-Chloropyrimidin-4-yl)-4-(2-fluoropropan-2-yl)oxazolidin-2-oneYield 57.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To the solution of 2,4-dichloropyrimidine (150 mg, 1.006 mmol) and 4-(2-fluoropropan-2-yl)oxazolidin-2-one (148 mg, 1.01 mmol) in DMF (4.5 mL), sodium hydride (60% wt. 89 mg, 2.21 mmol) was added to give a pale yellow mixture. The mixture was stirred at room temperature for 2 hr, diluted with EtOAc and stirred for additional 30 min. The separated organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine. The organic phase was dried over sodium sulfate, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 12 g, EtOAc/heptane=0/100 to 80/20] providing 3-(2-chloropyrimidin-4-yl)-4-(2-fluoropropan-2-yl)oxazolidin-2-one (150 mg) as a brown solid. MS m/z 260.1 (M+H)+; Rt-0.72 min. 1H NMR (400 Mhz, CDCl3) δ ppm 8.51 (d, J=5.9 Hz, 1H), 8.17 (d, J=5.9 Hz, 1H), 5.14 (dd, J=17.4, 8.0 Hz, 1H), 4.66 (d, J=9.4 Hz, 1H), 4.43-4.52 (m, 1H), 1.42-1.52 (m, 3H), 1.30-1.40 (m, 3H).

Workup

  1. customto give a pale yellow mixture
  2. stirringstirred for additional 30 min
  3. washThe separated organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
  4. dry with materialThe organic phase was dried over sodium sulfate
  5. filtrationfiltered off
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography [SiO2, 12 g, EtOAc/heptane=0/100 to 80/20]

Sources & evidence

ORD record
ord-fbba7dda150a4475ae1577e37631de99
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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