4-Aminotetrahydropyran → HCID 42630021, compound

Participants

Reaction Steps

A solution of trimethylaluminium (2 M in toluene, 600 μL, 1.2 mmol) was added dropwise (exothermic) to a solution of 4-aminotetrahydropyran (121 mg, 1.2 mmol) in dioxane (6 mL) and the resulting mixture was stirred at room temperature for 1 h. Then a solution of 6-(5-methyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester (102 mg, 0.3 mmol) in dioxane (3 mL) was added. The resulting mixture was heated at 85-95° C. for 5 h, cooled to room temperature, poured into a sodium potassium tartrate solution and extracted with ethyl acetate which was then washed with brine, dried over sodium sulfate and evaporated. Purification by chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (62 mg, 52%) which was obtained as a white solid after recrystallisation from ethylacetate:heptane. MS: m/e=396.3 [M+H]+.

Provenance & Evidence