Methyl iodide → 6-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16237Notes

Reaction equation

HRID 16237 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[Cl:7][C:8]1[N:13]=[C:12]([NH:14][C:15]2[CH:28]=[CH:27][C:18]3[C:19]([C:23]([NH:25][CH3:26])=[O:24])=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=2)[CH:11]=[CH:10][N:9]=1.CI>CC(C)=O>[Cl:7][C:8]1[N:13]=[C:12]([N:14]([CH3:1])[C:15]2[CH:28]=[CH:27][C:18]3[C:19]([C:23]([NH:25][CH3:26])=[O:24])=[C:20]([CH3:22])[O:21][C:17]=3[CH:16]=2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 592247466-(2-chloropyrimidin-4-ylamino)-N,2-dimethylbenzofuran-3-carboxamide

Product 1

HCID 592247476-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamideYield 22%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

Potassium carbonate (0.75 mmol) was added to a solution of 6-(2-chloropyrimidin-4-ylamino)-N,2-dimethylbenzofuran-3-carboxamide (0.5 mmol) in 5 ml acetone. After 15 mins, methyl iodide (0.5 mmol) was added. The reaction mixture was stirred at 60° C. for 2 days before the solvent was removed in vacuo. THF was added and the residue was filtered and subjected to column chromatography to provide the 6-((2-chloropyrimidin-4-yl)(methyl)amino)-N,2-dimethylbenzofuran-3-carboxamide in a yield of 22%.

Workup

  1. customwas removed in vacuo
  2. additionTHF was added
  3. filtrationthe residue was filtered

Sources & evidence

ORD record
ord-b08622b8d24847d484b646a4b84e3bf4
Source dataset
uspto-grants-2010_06
Patent number
US07737157B2

Reaction notes

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