Water → 5-Bromo-3-methyl-4(3H)-pyrimidinone

HRID 910609Notes

Reaction equation

HRID 910609 reaction equation
[Br:1][C:2]1[C:3](=[O:8])[NH:4][CH:5]=[N:6][CH:7]=1.[C:9](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:8])[N:4]([CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 882564(3H)-Pyrimidinone, 5-bromo-

Product 1

HCID 8246355-Bromo-3-methyl-4(3H)-pyrimidinoneYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromopyrimidin-4(3H)-one (578 mg) was dissolved in N,N-dimethylformamide (15 mL), and potassium carbonate (685 mg) and methyl iodide (247 μL) were added, followed by stirring at room temperature for 24 hours. Water was added to the reaction mixture, followed by extraction with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 5-bromo-3-methylpyrimidin-4(3H)-one (337 mg) as a white solid.

Workup

  1. extractionfollowed by extraction with chloroform
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-625a9a8e705a4040969997894f676f4c
Source dataset
uspto-grants-2011_09
Patent number
US08022208B2

Reaction notes

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