Ammonium Chloride → HCID 86723879, compound

Participants

Reaction Steps

To a solution of 3-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]propanoic acid (prepared in Example 73) (36.2 mg) in tetrahydrofuran (0.5 ml) was added under ice-cooling borane tetrahydrofuran complex (0.1 ml:1.09 M tetrahydrofuran solution), and the resulting mixture was stirred at room temperature for eighteen hours. The reaction mixture was cooled again under ice-cooling and thereto was added borane tetrahydrofuran complex (0.2 ml:1.09 M tetrahydrofuran solution) and the resulting mixture was stirred at room temperature for five hours. To the reaction mixture was added saturated aqueous ammonium chloride solution (2 ml) and the resulting mixture was extracted with ethyl acetate (20 ml×2). The organic layer was washed with water (20 ml) and saturated saline (20 ml), dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/methanol) to afford 4-[5-[3-(3-hydroxypropyl)-6-methyl-2,4-dioxo-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (26.2 mg).

Provenance & Evidence