N-Methylacetamide → HCID 59278270, compound

HRID 559733Notes

Reaction equation

HRID 559733 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](Cl)=[N:6][CH:7]=1.[H-].[Na+].[CH3:11][NH:12][C:13](=[O:15])[CH3:14]>C1COCC1.O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:12]([CH3:11])[C:13](=[O:15])[CH3:14])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6582N-MethylacetamideHCID 24758Sodium hydrideHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 59278270HCID 59278270, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-bromo-2-chloroprimidine (2.00 g, 10.34 mmol) in THF was added 60% NaH (0.34 g, 14.00 mmol) in mineral oil. After 20 minutes, N-methylacetamide (0.80 g, 11.00 mmol) was added dropwise. After 2 hours, the reaction was diluted with water and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel chromatography eluting with 30% ethyl acetate in heptane. The major fractions were combined and the solvent was concentrated in vacuo to afford N-(5-bromo-pyrimidin-2-yl)-N-methyl-acetamide.

Workup

  1. waitAfter 2 hours
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with 30% ethyl acetate in heptane
  8. concentrationthe solvent was concentrated in vacuo

Sources & evidence

ORD record
ord-8e51408291924bd1bd0b068c3e558774
Source dataset
uspto-grants-2011_11
Patent number
US08063065B2

Reaction notes

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