Sodium Hydroxide → 1-[(pyridin-2-yl)methyl]-1H-pyrazol-3-amine

Participants

Reaction Conditions

Reaction Steps

1.3 2-Chloromethylpyridine hydrochloride (1.0.9 mmol) is dissolved in water and NaOH (32% in water) is added and extracted with dichloromethane. The combined organic layers are dried over MgSO4 and the solvent is removed in vacuo. The remaining residue is added to a suspension of NaH (2 eq.) in DMF at 0° C. Afterwards 2-(1H-Pyrazole-3-yl)-isoindole-1,3-dione (11.7 mmol) is added and the reaction is stirred 15 hours at 50° C. The solvent is removed in vacuo. Hydrazine hydroxide (20 ml) and ethanol (20 ml) is added and the reaction is stirred 3 days at 120° C. The solvent is removed in vacuo and the residue is suspended in dichloromethane and filtrated. The solvent of the filtrate is removed in vacuo. The remaining residue is purified via column chromatography (ethyl acetate/methanol). 1-Pyridine-2-ylmethyl-1H-pyrazole-3-ylamine is isolated as a yellow powder in a yield of 20%; HPLC (Method B): 0.49 min; LC-MS: 0.550 min, 175.15 (M+H+);

Provenance & Evidence