Electric Literature of 1003-68-5 ,Some common heterocyclic compound, 1003-68-5, molecular formula is C6H7NO, its 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.
A solution of 5-methylpyridin-2(lH)-one, 1-495 (cas: 1003-68-5, 5.0 g, 45.87 mmol, 1.0 equiv.), KI (1.522 g, 9.17 mmol, 0.2 equiv.), and NaH (60%, 2.20 g, 55.04 mmol, 1.2 equiv.) in DMF (20 ml) was stirred under nitrogen at 0 C for 1 hour. Then the reaction mixture was added to a solution of /er/-butyl (2-bromoethyl)carbamate (cas: 39684-80-5, 15.34 g, 68.80 mmol, 1.5 equiv.) in DMF (30 mL) dropwise. The reaction mixture was stirred at 0 C for 1 hour and then 25 C for 12 hours. LCMS analysis showed -50% conversion, at which point H20 (50 mL) was added and the reaction mixture was extracted with EtOAc (100 mL x 3). The organic phase was dried and purified by silica gel chromatography (20%-50% EtOAc with Petroleum ether) to give the product /er/-butyl (2- (5-methyl-2-oxopyridin-l(2H)-yl)ethyl)carbamate, 1-496 (1.7 g, 15% yield, 95% purity) as a white solid, MS (ESI, positive ion) m/z: 253(M+l) and byproduct: tert-butyl (2-((5- methylpyridin-2-yl)oxy)ethyl)carbamate (0.4 g, 3% yield, 95% purity), MS (ESI, positive ion) m/z: 253(M+l).
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1003-68-5, its application will become more common.
Reference:
Patent; CARMOT THERAPEUTICS, INC.; ENQUIST, Johan; KRISHNAN, Shyam; ATWAL, Suman; ERLANSON, Daniel; FUCINI, Raymond V.; HANSEN, Stig; SAWAYAMA, Andrew; SETHOFER, Steven; (719 pag.)WO2019/183577; (2019); A1;,
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem