Extended knowledge of 59549-51-8

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.59549-51-8, name is 5-Bromo-2-chloro-4-(methylthio)pyrimidine, molecular formula is C5H4BrClN2S, molecular weight is 239.52, as common compound, the synthetic route is as follows.Quality Control of 5-Bromo-2-chloro-4-(methylthio)pyrimidine

A 3-L, 3-neck, round-bottom flask was equipped with a J-KEMtemperature controller, a mechanical stirrer, and a nitrogen inlet. The flask was charged with 5-bromo-2-chloro-4-(methylthio)pyrimidine (100 g, 417.5 mmol), (lr,4r)-4- aminocyclohexanol (76.4 g, 663.4 mmol), and ethanol (1 L). DIEA (109 mL,626.3 mmol) was added, and the mixture was heated to reflux overnight. TLC (1 : 1 hexanes/ethyl acetate) analysis after 20 h indicated complete reaction. The reaction was allowed to cool to room temperature. Water (300 mL) was added, and a precipitate gradually formed. The solid was filtered and washed with water to give 111.7 g of a white solid. The filtrate was extracted with ethyl acetate (3 x 300 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated to a semi-solid. The semi-solid was slurried in 1 : 1 hexanes/ethyl acetate and filtered to give an additional 12.1 g of a white solid. The two batches were combined to give 123.8 g (93%) of (lr,4r)- 4-(5-bromo-4-(methylthio)pyrimidin-2-ylamino)cyclohexanol as a white solid. MS (ESI) m/z 318, 320 [M+l]+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,59549-51-8, 5-Bromo-2-chloro-4-(methylthio)pyrimidine, and friends who are interested can also refer to it.

Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; BENNETT, Brydon, L.; ELSNER, Jan; ERDMAN, Paul; HILGRAF, Robert; LEBRUN, Laurie, Ann; MCCARRICK, Meg; MOGHADDAM, Mehran, F.; NAGY, Mark, A.; NORRIS, Stephen; PAISNER, David, A.; SLOSS, Marianne; ROMANOW, William, J.; SATOH, Yoshitaka; TIKHE, Jayashree; YOON, Won, Hyung; DELGADO, Mercedes; WO2012/145569; (2012); A1;,
Pyrimidine | C4H4N2 – PubChem,
Pyrimidine – Wikipedia