Ammonium Acetate → 1-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-ethanol

Participants

Reaction Steps

To a solution of 1-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-ethanone (150 mg, 0.493 mmol) in MeOH (5 mL) was added ammonium acetate (76 mg, 0.987 mmol). The reaction was stirred for 2 hours at room temperature. Sodium cyano borohydride (62 mg, 0.987) was added and the reaction was heated to 70° C. for 16 hours. LC-MS showed ˜1:1 ratio of alcohol and amine. The reaction was concentrated and purified by a reverse-phase C-18 preparative HPLC eluting with ACN—H2O having 0.1% acetic acid to give 1-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-ethanol (70 mg) and 1-(3-quinolin-6-ylmethyl-3H-[1,2,3]triazolo[4,5-b]pyrazin-5-yl)-ethylamine (20 mg).

Provenance & Evidence