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

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

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

customwas removed in vacuo
additionTHF was added
filtrationthe residue was filtered

Sources & evidence

ORD record: ord-b08622b8d24847d484b646a4b84e3bf4
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07737157B2

Linked notes

Loading…