Azetidine → 2-(2-(3-(azetidin-1-yl)-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine

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Reaction Steps

A solution of 2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (59 mg, 177 μmol, Eq: 1.00) in dioxane (2.11 ml) was purged with argon, then azetidine (15.1 mg, 17.8 μl, 265 μmol, Eq: 1.5), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (8.17 mg, 14.1 μmol, Eq: 0.08), tris(dibenzylideneacetone)dipalladium chloroform complex (7.31 mg, 7.06 μmol, Eq: 0.04) and sodium phenolate (20.5 mg, 177 μmol, Eq: 1.00) were added. The vial was capped and irradiated at 140° C. for 60 minutes in the microwave oven. Chromatography afforded 2-[2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,7-dimethyl-[1,2,4]triazolo[1,5-a]pyrimidine (15 mg/27.4%) as a light yellow solid. MS: m/z=311.4 (M+H+).

Provenance & Evidence