Synthesis of Aryl‐Substituted Pyrimidines by Site‐Selective Suzuki–Miyura Cross‐Coupling Reactions of 2,4,5,6‐Tetrachloropyrimidine

Abstract

Suzuki-Miyaura reactions of 2,4,5,6-tetrachloropyrimidine allow a convenient synthesis of mono-, di-, tri-and tetraarylpyrimidines which are not readily available by other methods. All reactions proceed with excellent site-selectivity.

Synthesis of Arylated Benzofurans by RegioselectiveSuzuki–Miyaura Cross‐Coupling Reactions of 2,3‐Dibromobenzofurans‐ and 2,3,5‐Tribromobenzofurans

“…The site‐selectivity is controlled by electronic and steric parameters . Recently, we have reported the synthesis of aryl‐substituted thiophenes , pyrroles , selenophenes , pyrimidines , and furans based on site‐selective Suzuki reactions of polyhalogenated heterocycles. In recent years, site‐selective Sonogashira , Negishi , and Stille coupling reactions of 2,3‐dibromobenzofuran and 2,6‐dibromobenzofuran have been studied.…”

Selective Palladium‐Catalyzed Suzuki–Miyaura Reactions of Polyhalogenated Heteroarenes

“…More recently, Hussain et al 173. synthesized some 6‐aryl‐2,4,5‐trichloropyrimidines 475 in high yields by PdCl 2 (PPh 3 ) 2 ‐catalyzed reaction of compound 473 with 1.0 equiv.…”

“…On the other hand, 4,6‐diaryl‐2,5‐dichloropyrimidines 476 were prepared in good‐to‐excellent yields and with excellent selectivity by PdCl 2 (PPh 3 ) 2 ‐catalyzed reaction of 473 with 2.0 equiv. of arylboronic acids in dioxane at 70 °C in the presence of 2 M K 2 CO 3 as the base (Scheme ) 173…”

Synthesis and Photophysical Properties of Alkynylated Pyrimidines by Site‐Selective Sonogashira Reactions of 2,4,5,6‐Tetrachloropyrimidine; First Synthesis of Tetraalkynyl‐pyrimidines

“…[9] Recently, we have reported the first Suzuki-Miyaura cross-coupling reactions of 2,4,5,6-tetrachloropyrimidine. [10] Herein, we report a series of reactions that constitute, to the best of our knowledge, the first Sonogashira reactions of 2,4,5,6-tetachloropyrimidine. All products, 4,6-dialkynyl-2,5-dichloropyrimidines, 2,4,6-trialkynyl-5-chloropyrimidines, and tetraalkynylpyrimidines, exhibit a fluorescence in the range of 395-470 nm.…”