Synthetic Route of 22536-61-4, 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 22536-61-4 as follows.
A 3 L 3-necked round bottom flask was fitted with a reflux condenser, a temperature controller and a septum and was charged with 2-chloro-5-methylpyrimidine (81 mL, 778 mmol), potassium vinyltrifluoroborate (156g, 1167 mmol), triphenylphosphine (18.02 mL, 78 mmol), cesium carbonate (156 mL, 1945 mmol) and a large stir bar. Water (1565 mL) was addedand the mixture was stirred for several mm and then THF (244 mL) was added. Argon was bubbled through the mixture for 5 mm and then palladium (II) chloride (1.72 g, 38.9 mmol) was added. The reaction was further sparged with argon for 5 mins. The temperature was raised to 62 °C and stirring was continued to completion. The reaction was then cooled to RT and filtered through two Whatman GF/F filter cups, rinsing with ether. The mixture was transferred to a separatory funnel, and the layers were separated. The aqueous layer was further extracted with diethyl ether (4 x 200 mL). The organic layers were combined and dried over anhydrous MgSO4 and then filtered. The mixture was partially concentrated on the rotory evaporator at 20 °C and 115 torr for an extended period of time to give an orange liquid. The material was further purified by Kugelrohr distillation to isolate the title compound (65.4g, 70percent) as a light yellow oil. 1H NMR (400 MHz, CDC13) oe 2.31 (s, 3H), 5.68 (d,J10.56 Hz, 1H), 6.55 (d,J17.22 Hz, 1H), 6.86 (dd,J17.41, 10.56 Hz, 1H), 8.54 (s, 2H). LCMS-ESI (pos.)m/z:121.1 (M+H)t
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,22536-61-4, its application will become more common.
Reference:
Patent; AMGEN INC.; CHEN, Yinhong; DRANSFIELD, Paul John; HARVEY, James S.; HEATH, Julie Anne; HOUZE, Jonathan; KHAKOO, Aarif Yusuf; KOPECKY, David J.; LAI, Su-Jen; MA, Zhihua; NISHIMURA, Nobuko; PATTAROPONG, Vatee; SWAMINATH, Gayathri; YEH, Wen-Chen; RAMSDEN, Philip Dean; (434 pag.)WO2018/93577; (2018); A1;,
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