5-(Azetidin-1-ylmethyl)-1-methyl-3-nitro-1H-pyrazole → 5-(Azetidin-1-ylmethyl)-1-methyl-1H-pyrazol-3-amine

Participants

Reaction Steps

A 500-mL Parr reactor bottle was purged with nitrogen and charged with 10% palladium on carbon (50% wet, 180 mg dry weight) and a solution of 21 (1.00 g, 5.10 mmol) in ethanol (100 mL). The bottle was attached to a Parr hydrogenator, evacuated, charged with hydrogen gas to a pressure of 50 psi and shaken for 2 h. After this time, the hydrogen was evacuated, and nitrogen was charged into the bottle. Celite 521 (1.0 g) was added, and the mixture was filtered through a pad of Celite 521. The filter cake was washed with ethanol (2×25 mL), and the combined filtrates were concentrated to dryness under reduced pressure to afford a 94% yield of 22 (800 mg) as a yellow oil: 1H NMR (300 MHz, CDCl3) δ 5.47 (s, 1H), 3.64 (s, 3H), 3.57 (br s, 2H), 3.43 (s, 2H), 3.19 (t, 4H, 0.1=7.2 Hz), 2.06 (quintet, 2H, J=7.2 Hz); MS (ESI+) m/z 167.1 (M+H).

Provenance & Evidence