5-Amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide → HCID 135985433, compound

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Reaction Steps

Into a 100-mL 3-necked round-bottom flask, was placed a solution of Na (64 mg, 2.78 mmol, 6.00 equiv) in ethanol (5 mL) at room temperature. To the resulting mixture was then added a solution of 5-amino-3-methyl-1-phenyl-1H-pyrazole-4-carboxamide (100 mg, 0.46 mmol, 1.00 equiv) in C4H10O (10 mL), in portions at room temperature, followed by a solution of ethyl 1-(pyridin-3-yl)piperidine-4-carboxylate (650 mg, 2.78 mmol, 6.00 equiv) in C4H10O (20 mL), in portions at room temperature. The resulting solution was heated to reflux for 5 hr. The reaction was then quenched by the addition of water (10 mL). The resulting solution was extracted with DCM (3×30 mL) and the organic layers combined. The resulting mixture was washed with sodium chloride (2×50 mL), then dried over anhydrous sodium sulfate. The solids were filtered out. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (50:1) to yield 3-methyl-1-phenyl-6-(1-(pyridin-3-yl)piperidin-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one as a white solid.

Provenance & Evidence