Methyl iodide → HCID 22281998, compound

Reaction equation

[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[C:3]=1[O:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[O:16][CH3:17].[C:18](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C)C=O>[CH3:18][O:8][C:4]1[C:3]([O:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[O:16][CH3:17])=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1

Participants

Procedure

A mixture of 5-amino-4-(2-methoxyphenoxy)-1-methyl-1,2-dihydro-3H-pyrazol-3-one (Preparation 69) (300 mg), caesium carbonate (1.25 g) and iodomethane (200 mg) in dry dimethylformamide (5 ml) was stirred under a nitrogen atmosphere for 24 hours at room temperature. The reaction mixture was partitioned between ethyl acetate (7×25 ml) and water (40 ml) and the combined organic extracts were dried (magnesium sulfate) and concentrated under vacuum. The residue was purified by chromatography on a Biotage Flash™ 40s silica cartridge (40 g silica) using neat ethyl acetate and then 1% methanol/dichloromethane as eluants to give the title compound as a brown solid (90 mg), Rf 0.57 (10% methanol/dichloromethane).