Methyl iodide → 6-Chloro-3-methylpyrimidin-4(3H)-one

HRID 237585

Reaction equation

HRID 237585 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.CI.[C:11]([O-])([O-])=O.[K+].[K+]>CC(C)=O>[Cl:1][C:2]1[N:7]=[CH:6][N:5]([CH3:11])[C:4](=[O:8])[CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1354454786-Chloropyrimidin-4-ol

Product 1

HCID 43664716-Chloro-3-methylpyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6-chloropyrimidin-4(3H)-one (5 g), methyliodide (2.6 mL) and K2CO3 (10.6 g) in acetone (100 mL) is stirred at room temperature over night. The mixture is partitioned between water and ethyl acetate. The organic phase is washed with brine, dried (MgSO4) and concentrated. The residue is triturated with diisopropylether to give the title compound. Yield: 5.1 g; LC (method 11): tR=0.25 min; Mass spectrum (ESI+): m/z=145 [M+H]+.

Workup

  1. customThe mixture is partitioned between water and ethyl acetate
  2. washThe organic phase is washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residue is triturated with diisopropylether

Sources & evidence

ORD record
ord-8455eaeb5462457094da2ec384ba5b7e
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Linked notes

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