Ammonia → HCID 86723873, compound

Participants

Reaction Steps

To a solution of 4-[5-[6-methyl-4-oxo-3-(2-oxoethyl)-1-(3-trifluoromethylphenyl)-1,2,3,4-tetrahydropyrimidin-5-yl]-1H-pyrazol-1-yl]benzonitrile (prepared in Example 68) (18.0 mg), ammonia (0.4 ml: 0.5 N tetrahydrofuran solution) and acetic acid (4 μl) in tetrahydrofuran (1.0 ml) was added sodium triacetoxyborohydride (11.9 mg) and the resulting mixture was stirred at room temperature for two hours. To the reaction mixture were added diisopropylethyl amine (48 μl) and acetic anhydride (78 μl) and the resulting mixture was stirred at 55° C. for two hours. To the reaction mixture was added water (20 ml) and the resulting mixture was extracted with ethyl acetate (20 ml×2). The organic layer was washed with water (10 ml) and saturated saline (10 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 N-[2-[5-[1-(4-cyanophenyl)-1H-pyrazol-5-yl]-4-methyl-2,6-dioxo-3-(3-trifluoromethylphenyl)-2,3-dihydropyrimidin-1(6H)-yl]ethyl]acetamide (7.6 mg).

Provenance & Evidence