1,4-Dioxane → 2-(4-[1,2,3]Triazol-1-yl-butyl)-pyrimidine-5-boronic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of tris(dibenzylideneacetone)dipalladium(0) (0.027 g, 0.03 mmol in dioxane (6 ml) tricyclohexylphosphine (0.084 g, 0.30 mmol) is added and the mixture stirred under argon for 30 min. A solution of 5-bromo-2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine (0.282 g, 1.0 mmol), bis(pinacolato)diboron (0.279 g, 1.1 mmol) and potassium acetate (0.147 g, 1.5 mmol) is added and the mixture is heated at 80° C. for 5 h. After cooling the mixture is concentrated in vacuo and the crude product is purified by flash column chromatography (ethyl acetate (100%)->ethyl acetate/tetrahydrofuran 1:1) yielding 2-(4-[1,2,3]triazol-1-yl-butyl)-pyrimidine-5-boronic acid as a beige solid. Yield 140 mg (57%).

Provenance & Evidence