Sodium hydride → 4-(2-Methyloxiran-2-yl)pyrimidine

HRID 1401572Notes

Reaction equation

HRID 1401572 reaction equation
[I-].[CH3:2][S+](C)C.[H-].[Na+].[C:8]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][N:12]=1)(=[O:10])[CH3:9]>CN(C=O)C.CS(C)=O>[CH3:9][C:8]1([C:11]2[CH:16]=[CH:15][N:14]=[CH:13][N:12]=2)[CH2:2][O:10]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 5380601-(Pyrimidin-4-yl)ethanone

Product 1

HCID 594549674-(2-Methyloxiran-2-yl)pyrimidineYield 54.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6228DimethylformamideSolvent

Procedure

Trimethylsulfonium iodide (3.34 g, 16.3 mmol) was dissolved in DMF (20 mL) and stirred at RT for 5 min. Sodium hydride (600 mg, 25 mmol) was added portionwise at the same temperature and stirred for 15 min. 4-Acetyl pyrimidine (1 g, 8.1 mmol) in 0.5 mL DMSO was added dropwise and the reaction mixture stirred for 1 h. After completion of reaction, the mixture was poured into ice-cold water and extracted with Ether (3×). The combined organic layer was washed with water several times followed by brine, and dried over sodium sulfate, then evaporated to provide 600 mg of 4-(2-Methyl-oxiranyl)-pyrimidine. 1H NMR (CDCl3, freebase) δ (ppm): 9.15 (s, 1H), 8.7 (d, 1H), 7.35 (d, 1H), 2.95 (d, 1H), 2.88 (d, 1H), 1.8 (s, 3H).

Workup

  1. stirringstirred for 15 min
  2. stirringthe reaction mixture stirred for 1 h
  3. customAfter completion of reaction
  4. additionthe mixture was poured into ice-cold water
  5. extractionextracted with Ether (3×)
  6. washThe combined organic layer was washed with water several times
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-a298b9b653f04a2abe2191b989b3f332
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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