Ethylene Glycol → HCID 86640819, compound

Participants

Reaction Conditions

Reaction Steps

5-((Tetrahydro-2H-pyran-4-yl)methyl)[1,2,4]triazolo[1,5-a]pyridin-2-amine. To a solution of (2-amino-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (8 g, 32.5 mmol) in ethylene glycol (100 mL) was added hydrazine monohydrate (8.16 mL, 260 mmol) and the reaction mixture was stirred for 5 min until a clear solution was obtained. Solid potassium hydroxide (3.65 g, 65.0 mmol) dissolved in ethylene glycol (20 mL) was added and the reaction mixture was heated at 160° C. for 16 h. Water (100 mL) was added to the reaction, and it was neutralized to pH=7 with hydrochloric acid. The reaction was then extracted with ethyl acetate (2×400 mL). The combined organics were dried over magnesium sulfate, filtered, concentrated on a rotary evaporator to give the desired product (7 g, 30.1 mmol, 93% yield) as an off white solid. MS (ESI) m/z 233.2 [M+1]+. This material was used without further purification in the next step.

Provenance & Evidence