Application
2-Chloro-5-phenylpyrimidine can be used as an organic synthesis intermediate. It can be prepared by reacting 5-bromo-2-chloropyrimidine with Ph3In as a reactant, or by reacting 5-bromo-2-chloropyrimidine with phenylboronic acid via the Suzuki reaction.
Synthesis
General procedure: 5-bromo-2-chloropyrimidine (1 eq.), phenylboronic acid (1.1 eq.), Na2CO3 (1.1 eq.) and H2O (5 mL) were added to a round bottom flask, followed by catalyst (2 mol%). The reaction mixture was stirred at 45 °C until the reaction was complete. Upon completion of the reaction, the reaction mixture was diluted with water and the product was extracted with ethyl acetate. The ethyl acetate extract was filtered through a bed of diatomaceous earth and subsequently analyzed by GC. Retention times were verified using standards of 5-bromo-2-chloropyrimidine and 2-chloro-5-phenylpyrimidine to confirm product generation. The ethyl acetate extract was concentrated and purified by silica gel column chromatography using a solvent mixture of hexane and ethyl acetate as eluent to give 2-chloro-5-phenylpyrimidine. The product was characterized by NMR, GC-MS and UPLC analysis.
References
[1] Journal of Heterocyclic Chemistry, 2008, vol. 45, # 4, p. 1077 - 1081
[2] Journal of Molecular Catalysis A: Chemical, 2013, vol. 371, p. 118 - 124
[3] European Journal of Medicinal Chemistry, 2018, vol. 150, p. 30 - 38
[4] Patent: WO2004/22556, 2004, A1. Location in patent: Page 16-17
