Methyl iodide → HCID 86697274, compound

HRID 237605Notes

Reaction equation

HRID 237605 reaction equation
[I:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([C:9]2[CH:14]=[CH:13][NH:12][C:11](=[O:15])[N:10]=2)=[CH:4][C:3]=1[CH3:16].CI.[C:19]([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[I:1][C:2]1[C:3]([CH3:16])=[CH:4][C:5]([C:9]2[CH:14]=[CH:13][N:12]([CH3:19])[C:11](=[O:15])[N:10]=2)=[CH:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178422842HCID 178422842, compound

Product 1

HCID 86697274HCID 86697274, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 4-(4-iodo-3,5-dimethylphenyl)pyrimidin-2(1H)-one (500 mg), methyliodide (165 μL) and K2CO3 (254 mg) in N,N-dimethylformamide (10 mL) is stirred for 12 hours at room temperature. Then the mixture is partitioned between water and dichloromethane. The aqueous phase is extracted twice with dichloromethane and the combined organic phases are washed with brine. After drying (MgSO4) the solvents are evaporated. The residue is triturated with diethylether. The solid is filtered off and dried to give the title compound. Yield: 380 mg; LC (method 11): tR=0.96 min; Mass spectrum (ESI+): m/z=341 [M+H]+.

Workup

  1. customThen the mixture is partitioned between water and dichloromethane
  2. extractionThe aqueous phase is extracted twice with dichloromethane
  3. washthe combined organic phases are washed with brine
  4. dry with materialAfter drying (MgSO4) the solvents
  5. customare evaporated
  6. customThe residue is triturated with diethylether
  7. filtrationThe solid is filtered off
  8. customdried

Sources & evidence

ORD record
ord-13f58dcdbd7f4056bef51de82dad46ec
Source dataset
uspto-grants-2014_02
Patent number
US08642585B2

Reaction notes

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