Azetidine → 2-[(E)-2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine

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Reaction Steps

A solution of (E)-2-(2-(3-bromo-1-methyl-1H-1,2,4-triazol-5-yl)vinyl)-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine (150 mg, 449 μmol, Eq: 1.00) in dioxane (210.4 ml) was purged with argon, then sodium phenolate (78.2 mg, 673 μmol, Eq: 1.5), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (xant-phos) (20.8 mg, 35.9 μmol, Eq: 0.08), tris(dibenzylideneacetone)-dipalladium chloroform complex/Pd2(dba)3CHCl3 (18.6 mg, 18.0 μmol, Eq: 0.04) and azetidine (76.9 mg, 90.5 μl, 1.35 mmol, Eq: 3) were added. The vial was capped and irradiated at 140° C. for 40 minutes in a microwave oven. The crude material was applied on silica gel and purified by flash chromatography over a 20 g silica gel column using ethyl acetate/methanol 0-10% as eluent affording 2-[(E)-2-(5-azetidin-1-yl-2-methyl-2H-[1,2,4]triazol-3-yl)-vinyl]-5,8-dimethyl-[1,2,4]triazolo[1,5-c]pyrimidine (89 mg, 63.9%) as light yellow solid. MS: m/z=311.5 (M+H+), MP: 210.4° C.

Provenance & Evidence