Methyl iodide → 5-bromo-1-methylpyrimidin-2(1H)-one

HRID 237588Notes

Reaction equation

HRID 237588 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.CI.[C:11]([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[Br:1][C:2]1[CH:3]=[N:4][C:5](=[O:8])[N:6]([CH3:11])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1014945-Bromo-2(1H)-pyrimidinone

Product 1

HCID 1397075-bromo-1-methylpyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 5-bromopyrimidin-2(1H)-one (3 g), methyliodide (1.1 mL) and K2CO3 (2.4 g) in N,N-dimethylformamide (60 mL) is stirred for 5 hours at room temperature. The mixture is filtered and the mother liquor is concentrated. The residue is partitioned between water and dichloromethane. The organic phase is washed with brine, dried (MgSO4) and concentrated to give the title compound. Yield: 385 mg; LC (method 9): tR=0.25 min; Mass spectrum (ESI+): m/z=189 [M+H]+.

Workup

  1. filtrationThe mixture is filtered
  2. concentrationthe mother liquor is concentrated
  3. customThe residue is partitioned between water and dichloromethane
  4. washThe organic phase is washed with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-da26afe45c084e588889ca5a8671f02c
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

Loading…