Sodium hydride → HCID 86730141, compound

HRID 1850113Notes

Reaction equation

HRID 1850113 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][O:5][C:4](=[O:7])[NH:3]1.[Cl:9][C:10]1[N:15]=[C:14](Cl)[CH:13]=[C:12]([Cl:17])[N:11]=1.[H-].[Na+]>CN(C=O)C.CCOC(C)=O>[Cl:9][C:10]1[N:15]=[C:14]([N:3]2[C:2]([CH3:8])([CH3:1])[CH2:6][O:5][C:4]2=[O:7])[CH:13]=[C:12]([Cl:17])[N:11]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 773782,4,6-TrichloropyrimidineHCID 1413154,4-Dimethyl-1,3-oxazolidin-2-one

Product 1

HCID 86730141HCID 86730141, compoundYield 62.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4,4-dimethyloxazolidin-2-one (0.103 g, 0.895 mmol) and 2,4,6-trichloropyrimidine (0.181 g, 0.984 mmol, 1.10 equiv) in DMF (3 mL) was treated with NaH (60%, 0.0429 g, 1.07 mmol, 1.2 equiv), then the resulting mixture (yellow) was stirred at room temperature for 1 h. The reaction mixture was diluted with EtOAc (20 mL), washed with saturated aqueous NaCl (2×20 mL), dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 0 to 40%) provided 3-(2,6-dichloropyrimidin-4-yl)-4,4-dimethyloxazolidin-2-one (0.146 g, white solid) in 62.3% yield. 1H NMR (300 MHz, CDCl3) δ 8.14 (s, 1H), 4.16 (s, 2H), 1.74 (s, 9H); LCMS m/z 261.9 (M+H)+, Rt 0.91 min.

Workup

  1. washwashed with saturated aqueous NaCl (2×20 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-9c2e71c85daf446fab803a21bda3fa24
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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