4-Methylmorpholine → 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(hydroxymethyl)-1H-pyrazol-1-yl)benzonitrile

Participants

Reaction Steps

To a solution of 1-(4-cyanophenyl)-5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-1H-pyrazole-4-carboxylic acid (prepared in Example 132) (100 mg) and N-methylmorpholine (66 μL) in tetrahydrofuran (2 ml) was added at 0° C. isobutyl chloroformate (79 μl). After thirty minutes, to the reaction mixture was added sodium borohydride (26.4 mg) and the resulting mixture was stirred for three and a half hours. Thereto was added sodium borohydride (55.6 mg) and the mixture was stirred for another thirty minutes and thereto were added water and saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline and then dried over sodium sulfate, and then concentrated on evaporator instrument. The residue was purified by silica gel column chromatography to afford the intended 4-(5-(3,6-dimethyl-2,4-dioxo-1-(3-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydropyrimidin-5-yl)-4-(hydroxymethyl)-1H-pyrazol-1-yl)benzonitrile.

Provenance & Evidence