4-Chloro-2,6-diphenylpyrimidine

Chemical Properties

White solid

Synthesis Reference(s)

Journal of Medicinal Chemistry, 47, p. 6529, 2004 DOI: 10.1021/jm049448r

Synthesis

Using 2,4,6-trichloropyrimidine (10 g, 54.5 mmol) and (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzene (22.3 g, 109 mmol) as raw material, catalyzed by tetrakis(triphenylphosphine)palladium (3.8 g, 3.27 mmol) in a mixed solvent of THF (240 mL) and water (120 mL). Potassium carbonate (45.2 g) was added and the reaction was stirred at 90 °C. Upon completion of the reaction, extraction was carried out with dichloromethane and water. The organic layer was dried with anhydrous magnesium sulfate and concentrated. Purified by silica gel column chromatography and recrystallization, 9.5 g of 4-chloro-2,6-diphenylpyrimidine was obtained in 65% yield.

References

[1] Patent: KR2017/127593, 2017, A. Location in patent: Paragraph 0400-0402
[2] Patent: KR2017/120233, 2017, A. Location in patent: Paragraph 0511; 0512
[3] Patent: US2018/251473, 2018, A1. Location in patent: Paragraph 0253; 0254
[4] Patent: US2018/282276, 2018, A1. Location in patent: Paragraph 0222; 0223