Synthesis Reference(s)
The Journal of Organic Chemistry, 53, p. 4137, 1988
DOI: 10.1021/jo00252a057
Synthesis
General procedure for the synthesis of 2-chloro-4-phenylpyrimidines from 2,4-dichloropyrimidines and phenylboronic acid: first, 2,4-dichloropyrimidines (5 g, 33.57 mmol) were dissolved in acetonitrile (60 ml), followed by the addition of water (15 ml). Next, phenylboronic acid (4.09 g, 33.57 mmol) and sodium carbonate (14.23 g, 134.28 mmol) were added to this solution. Degassing was carried out by blowing nitrogen into the reaction mixture for 10 minutes. After that, tetrakis(triphenylphosphine)palladium (354 mg, 0.34 mmol) was added. The reaction mixture was stirred under nitrogen protection at 90 °C for 18 hours. After completion of the reaction, the mixture was filtered through diatomaceous earth and the filtrate was collected. The solvent was removed by distillation under reduced pressure and the crude product obtained was purified by column chromatography with the eluent being a 10-15% ethyl acetate/petroleum ether solvent mixture, resulting in the target compound 2-chloro-4-phenylpyrimidine as a colorless solid (2.98 g, 47% yield). Mass spectrum (LRMS) [M + H]+ m/z: 191.1; 1H NMR (400 MHz, CDCl3) δ 8.62 (d, J = 5.3 Hz, 1H), 8.16-7.99 (m, 2H), 7.63 (d, J = 5.3 Hz, 1H), 7.50 (qdd, J = 6.0,3.2,1.4 Hz, 3H).
References
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