HCID 60886989, compound → 1-(4-amino-1H-pyrazol-1-yl)-2-methylpropan-2-ol

Participants

Reaction Steps

2-methyl-1-(4-nitro-1H-pyrazol-1-yl)propan-2-ol (2.0 g, 10.8 mmol) was dissolved in MeOH (50 mL) and 10% Pd/C (240 mg) was added. A hydrogen balloon was fitted over the reaction and the reaction was allowed to stir at rt for 16 hrs. The reaction was checked using the polar APCI method and LCMS showed 70% complete with 30% starting material remaining. Another 200 mg of 10% Pd/C was added and the balloon was re-charged with fresh hydrogen. After 4 hrs, the reaction was complete. The reaction was filtered through Celite, washing with MeOH (three×50 mL) and the combined filtrate was concentrated to dryness. Purification was accomplished via flash chromatography eluting with gradient of 3%-20% MeOH in DCM. The pure fractions were pooled and concentrated to afford the title compound (1.4 g, 84% yield) as a purple solid. 1H NMR (400 MHz, chloroform-d) δ ppm 1.14 (s, 6H), 3.92 (s, 2H), 7.04 (s, 1H), 7.19 (s, 1H); m/z (APCI+) for C7H13N3O 156.0 (M+H)+.

Provenance & Evidence