Electric Literature of 14001-67-3, In the chemical reaction process,reaction time,type of solvent,can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product.An updated downstream synthesis route of 14001-67-3 as follows.
To a 100 mL one neck round bottom flask was charged with 2-methylthio-5- bromopyrimidine (1 g, 4.88 mmol) along with pinacoldiborane (1.362 g, 5.36 mmol), potassium acetate (0.957 g, 9.75 mmol), Pd(dppf)CH2C12 (0.178 g, 0.244 mmol) and DMSO (10 ml). The flask was sealed with septum and connected to manifold through a syringe needle. The system was vacuumed and refilled with nitrogen three times and the mixture wasthen stirred and heated in an oil bath of 100 OC for 6 hr. The reaction mixture was black. LCMS showed complete consumption of starting material. After cooled to room temperature, the residue was diluted with ethyl acetate (100 mL) and water (50 ml). The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3x). The combined organic phases were washed with water, dried over Mg504, filtered and concentrated. The residue waspurified by MPLC (24 g silica gel, 10 to 60% ethyl acetate in hexanes) to afford ligh yellow solid product 2-(methylsulfanyl)-5 -(4,4,5,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)pyrimidine. LC-MS (ES, m/z): C11H17BN2025: 252; Found: 253 [M+H]+.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,14001-67-3, its application will become more common.
Reference:
Patent; MERCK SHARP & DOHME CORP.; DEVITA, Robert, J.; YU, Yang; LIU, Jian; HE, Shuwen; KRIKORIAN, Arto, D.; MILLER, Daniel, J.; WU, Zhicai; YANG, Ginger Xu-Qiang; HONG, Quingmei; LAI, Zhong; ZORN, Nicolas; TING, Pauline, C.; WO2013/130370; (2013); A2;,
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