Electric Literature of 4774-14-5, 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 4774-14-5 as follows.
2,2,6,6-tetramethylpiperidine (2.84 g, 20.1 mmol) in THF (250 mL) at -100C was added n-butyllithium (13.8 mL, 22.1 mmol). The solution was stirred for 20 minutes and cooled to -90C. 2,6-Dichloropyrazine (3.0 g, 20.1 mmol) in THF (10 mL) was added to the solution followed by carbon dioxide (89 g, 2014 mmol) as dry ice powder. The mixture was then allowed to warm to room temperature while stirring. The reaction mixture was concentrated under reduced pressure, diluted with water (20OmL) and acidified with 10% aq. HCl solution to pH 2. Extraction with EtOAc (x3) was followed by extraction with saturated aq. NaHCO3 solution. The aquous solution was acidified carefully with 10% aq. HCl solution to pH 2. The solution was extracted with EtOAc(x3) and the resulting solution was washed with water and brine. The organics were dried over anhydrous MgSO4 and concentrated. The resulting solid was trituated with Hex/chloroform (1 :1) and the remaining solid was filtered and washed with hexane to provide the title compound as an off-white solid (1.78 g, 9.22 mmol, 45.8% yield); IH NMR (400 MHz, DMSO-J6) delta ppm 8.90 (s, 1 H).
According to the analysis of related databases, 4774-14-5, the application of this compound in the production field has become more and more popular.
Reference:
Patent; SIGNAL PHARMACEUTICALS, LLC; WO2009/89042; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem