吡那考
硼酸化
硼酸
化学
产量(工程)
铃木反应
胺气处理
组合化学
硅烷化
有机化学
卤素
催化作用
芳基
钯
冶金
材料科学
烷基
作者
Nitinchandra D. Patel,Yongda Zhang,Jun Gao,Kanwar Sidhu,Jon C. Lorenz,Keith R. Fandrick,Jason A. Mulder,Melissa A. Herbage,Zhibin Li,Shengli Ma,Heewon Lee,Nelu Grinberg,Jinhua J. Song,Carl A. Busacca,Nathan K. Yee,Chris H. Senanayake
标识
DOI:10.1021/acs.oprd.5b00360
摘要
A practical and cost-effective synthesis of (2-aminopyrimidin-5-yl) boronic acid 1b has been developed. Key features of the synthesis include the inexpensive in situ protection of the amine via bis-silylation using TMSCl followed by metal–halogen exchange using n-BuLi and trapping with B(Oi-Pr)3. The water-soluble boronic acid is isolated by a well-designed acid–base sequence providing the target in 80% yield and high purity for the two-step process. The large-scale (15 kg) implementation of a Suzuki–Miyaura borylation to form the pinacol boronic ester is also described.
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