Potassium Carbonate → 2-[5-(9,9-Dimethylfluoren-2-yl)-4'-(2-pyridyl)biphenyl-3-yl]-4,6-diphenylpyrimidine

Participants

Reaction Steps

In a stream of argon, 0.71 g (3 mmol) of 9,9-dimethyl-2-fluoreneboronic acid, 1.4 g (3 mmol) of 2-(3,5-dibromophenyl)-4,6-diphenylpyrimidine and 34.7 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium were suspended in a mixed solvent composed of 115 mL of toluene and 15 mL of ethanol, and the resultant suspension was heated to 50° C. To the suspension, 9 mL (9 mmol) of an aqueous 1M K2CO3 solution was gradually added dropwise, and the mixture was stirred for 18 hours. The resultant reaction mixture was cooled to room temperature, and then, 0.896 g (4.5 mmol) of 4-(2-pyridyl)phenylboronic acid and 9 mL (9 mmol) of an aqueous 1M K2CO3 solution were added to the reaction mixture. The resultant mixture was heated to 60° C., and maintained at that temperature for 3.5 hours while being stirred. The obtained reaction mixture was cooled to room temperature, and then distilled under a reduced pressure to remove all volatile materials. Methanol was added to the concentrate, and the thus-deposited solid was collected by filtration. The obtained crude product was purified by silica gel chromatography using a hexane/chloroform (1:2) mixed solvent as an eluent to give 0.85 g of the target 2-[5-(9,9-dimethylfluoren-2-yl)-4′-(2-pyridyl)biphenyl-3-yl]-4,6-diphenylpyrimidine as a white solid (yield: 43.3%).

Provenance & Evidence