Water → HCID 86723913, compound

Participants

Reaction Steps

To a solution of 4-(5-(3-ethyl-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(2-hydroxypropan-2-yl)-1H-pyrazol-1-yl)benzonitrile (prepared in Example 288) (114.7 mg) in chloroform (1.0 ml) was added at room temperature sodium azide (28.4 mg) and trifluoroacetic acid (200 μl) and the resulting mixture was stirred at room temperature for sixteen hours. The reaction mixture was diluted with ethyl acetate (30 ml) and the organic layer was dried over anhydrous sodium sulfate and then concentrated under reduced pressure to afford the residue. To a solution of the obtained residue in acetic acid (1.0 ml) were added at room temperature zinc dust (143.2 mg) and water (200 μl) and the resulting mixture was stirred at room temperature for eight hours. The reaction mixture was diluted with ethyl acetate (30 ml) and the solids were then filtered, and the organic layer was washed with saturated aqueous sodium hydrogen carbonate solution (10 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-(4-(2-aminopropane-2-yl)-5-(3-ethyl-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazol-1-yl)benzonitrile (51.8 mg). UPLC/MS 523 (M+H)/0.73 min. (measurement condition 9)

Provenance & Evidence