Electric Literature of 106-65-0,Some common heterocyclic compound, 106-65-0, name is Dimethyl succinate, molecular formula is C6H10O4, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
Synthesis of 5-Methoxycarbonylmethyl-2-thiouracil (181): A mixture of sodium methoxide (13.5 g, 0.25 mol) in 200 mL of diethyl ether was cooled to 0 00 and it was added slowly to a stirred mixture ofdimethyl succinate 178 (36.5 g, 0.25 mol) and ethyl formate (18.5 g, 0.25 mol). The reaction mixture was stirred at 0 CC for 3 h, and at room temperature overnight. The solvent was evaporated, and the residue was washed thoroughly with petroleum ether resulting intermediate 180. The crude intermediate 180 was dissolved in methanol, and 19 g (0.25 mol) of thiourea was added. The reaction mixture was refluxed overnight. It was filtered, and the solid was washed with methanol. The filtrate was concentrated underreduced pressure. Flash chromatographic purification on a silica gel column resulting in the desired product 181 in 20% yield.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Dimethyl succinate, its application will become more common.
Reference:
Patent; MODERNA THERAPEUTICS, INC.; ROY, Atanu; CONLEE, Christopher, R.; DE FOUGEROLLES, Antonin; FRALEY, Andrew, W.; (766 pag.)WO2015/196130; (2015); A2;,
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