Potassium Carbonate → HCID 86712914, compound

Participants

Reaction Steps

A solution of the compound (1.39 g, 2.5 mmol) obtained in Example 16-5), 4,6-dichloropyrimidine (1.49 g, 10 mmol), tetrakis(triphenylphosphine)palladium(0) (577 mg, 0.5 mmol), and potassium carbonate (691 mg, 5 mmol) in dimethoxyethane (10 mL) and water (2.5 mL) was stirred at 130° C. for 1.5 h under microwave irradiation. The reaction mixture was cooled to room temperature, saturated aqueous sodium hydrogencarbonate was added to the reaction mixture, the mixture was extracted with dichloromethane, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, a solution of 4 M hydrochloric acid (1,4-dioxane solution, 2.5 mL) in methanol (10 mL) was added to the residue, and the mixture was stirred at room temperature for 16 h. The reaction mixture was concentrated under reduced pressure, saturated aqueous sodium hydrogencarbonate was added to the residue, the mixture was extracted with dichloromethane, and the organic layer was washed with saturated sodium chloride solution and dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (Isco Combiflash, 12 g, methanol:ethyl acetate=0:100 to 40:60, gradient) to obtain the title compound (551 mg, 52%) as a colorless solid.

Provenance & Evidence