N,N-Dimethylethylenediamine → 5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

To a solution of the compound prepared in Example 269 (2.84 g) in dimethyl sulfoxide (9.8 ml) were added methanesulfinic acid sodium (2.00 g), copper trifluoromethanesulfonate benzene complex (1.24 g), N,N-dimethylethylenediamine (529 mg) and the resulting mixture was stirred at 110° C. for seven hours. The reaction mixture was diluted with ethyl acetate (300 ml), and the organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate) to afford 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl-4-(methylsulfonyl)-1H-pyrazol-1-yl)benzonitrile (1.25 g).

Provenance & Evidence