Synthesis
General procedure for the synthesis of 2-phenylpyrimidine from 2-chloropyrimidine and phenylboronic acid: 2-chloropyrimidine (0.50 g, 4.37 mmol), phenylboronic acid (0.69 g, 5.68 mmol), sodium carbonate (Na2CO3, 0.92 g, 8.70 mmol), palladium dichloride (PdCl2, 38.7 mg, 0.22 mmol) and 1,4-bis(diphenylphosphino)butane (dppb, 92.9 mg, 0.22 mmol). The air in the reaction system was displaced with nitrogen for 10 min, followed by the addition of a predegassed solvent mixture of toluene (12 mL), water (6 mL) and ethanol (2 mL). The reaction mixture was stirred at 100 °C for 20 hours. Upon completion of the reaction, the mixture was filtered through a pad of diatomaceous earth and the filtrate was concentrated under reduced pressure to remove the volatile solvent. The crude product was purified by silica gel column chromatography with the eluent being a solvent mixture of 10% ether/dichloromethane, resulting in a white solid product in 65% yield. The spectral data of the product were in agreement with those reported in the literature.
References
[1] European Journal of Organic Chemistry, 2010, # 23, p. 4376 - 4380
[2] Chemical Communications, 2014, vol. 50, # 91, p. 14129 - 14132
[3] Organic and Biomolecular Chemistry, 2013, vol. 11, # 17, p. 2756 - 2760
[4] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259,12
[5] European Journal of Organic Chemistry, 2012, # 31, p. 6248 - 6259
