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

Temperature

110 °C

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).

1. washthe organic layer was washed with 10% ammonia water (50 ml) and saturated saline (50 ml)
2. dry with materialdried over anhydrous sodium sulfate
3. concentrationconcentrated under reduced pressure
4. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate)

ORD record

ord-35e5bd401da64b9c8d637d157f70b4fa

Source dataset

uspto-grants-2015_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09040516B2