Synthesis
At room temperature and under argon atmosphere, 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bis(1,3,2-dioxaborhexacyclopentane) (1.77 g, 6.95 mmol), potassium acetate (1.36 g, 13.90 mmol), and palladium diacetate (104 mg, 0.463 mol) were added to a stirred solution of 5-bromo-2-(methylthio)pyrimidine (950 mg, 4.63 mmol) in DMF (5 mL). The resulting suspension was degassed with argon for 15 min and then heated overnight at 85 °C. The reaction mixture was cooled to room temperature. EtOAc (10 mL) was added to the reaction mixture, and the reaction mixture was washed with brine (15 mL x 3). The organic phase was dried (MgSO4), filtered, and concentrated.
Application
Studies have reported that 2-methylthiopyrimidine-5-boronic acid pinaester can be used to prepare the following intermediate, which can be used to prepare substituted imidazo[1,2-a]pyridine derivatives.
