Application of 22536-61-4, Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps,and cheap raw materials. 22536-61-4, name is 2-Chloro-5-methylpyrimidine. A new synthetic method of this compound is introduced below.
To a 500 mL RBF was added 2-chloro-5-methylpyrimidine (12 g, 93 mmol), potassium (E)- trifluoro(prop-1-en-1-yl)borate (17.27 g, 117 mmol), and potassium phosphate (59.4 g, 280 mmol). The flask was purged with N2(5x) and then 1,4-dioxane (200 mL) and water (20 mL) were added. The resulting yellow suspension was sparged with Ar for 15 min and then 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (Amphos, commercially available from Strem, 2.64 g, 3.73 mmol) was added, a reflux condenser was attached, and the reaction was warmed to 90 C in an oil bath and stirred under N2for 16.5 h. The reaction was then cooled to RT. The reaction was diluted with water (250 mL) and extracted with EtOAc (2 x 250 mL). The organic layers were combined, dried (MgSO4), and concentrated. The residue was purified by flash chromatography on silica gel eluting with 0-20% EtOAc/hexanes) to afford (E)-5-methyl-2-(prop-1-en-1- yl)pyrimidine 466.01 (12.96 g, 97 mmol, 100% yield) as a yellow/orange oily solid.1H NMR (300 MHz, CDCl3) delta 8.49 (s, 2H), 7.01-7.20 (m, 1H), 6.57 (dd, J= 15.6, 1.7 Hz, 1H), 2.29 (s, 3H), 1.97 (dd, J= 6.8, 1.6 Hz, 3H). LCMS (ESI pos.) m/z: 135.2 (M+H)+.
At the same time, in my other blogs, there are other synthetic methods of this type of compound,22536-61-4, 2-Chloro-5-methylpyrimidine, and friends who are interested can also refer to it.
Reference:
Patent; AMGEN INC.; CHEN, Ning; CHEN, Xiaoqi; CHEN, Yinhong; CHENG, Alan C.; CONNORS, Richard V.; DEIGNAN, Jeffrey; DRANSFIELD, Paul John; DU, Xiaohui; FU, Zice; HARVEY, James S.; HEATH, Julie Anne; HEUMANN, Lars V.; HORNE, Daniel B.; HOUZE, Jonathan; KALLER, Matthew R.; KAYSER, Frank; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; MEDINA, Julio C.; MIHALIC, Jeffrey T.; NISHIMURA, Nobuko; OLSON, Steven H.; PATTAROPONG, Vatee; SWAMINATH, Gayathri; WANG, Xiaodong; WANSKA, Malgorzata; YANG, Kevin; YEH, Wen-Chen; (700 pag.)WO2018/97945; (2018); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia