Synthetic Route of 55557-52-3,Some common heterocyclic compound, 55557-52-3, name is 3-Chloropyrazine-2-carbonitrile, molecular formula is C5H2ClN3, 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.
To a solution of 3-chloropyrazine-2-carbonitrile 14 (4.60 g,32.96 mmol) in EtOH (120 mL) was added NaSH (3.94 g,42.79mmol), and themixture was stirred at roomtemperature for 3 h (TLC monitoring). EtOH was evaporated under reduced pressure,and the residue was dissolved in H2O and 2 M HCl was carefully added to neutralize the suspension. After evaporation of the solvent, the residue was dissolved in acetone (48 mL) and ClCH2CN (2.29 mL, 32.96 mmol), K2CO3 (4.55 g, 32.96 mmol), and a catalytic amount of KI were added. The resulting mixture was stirred at room temperature for 3 h, and then the resulting residue was separated by filtration and washed with acetone (3 30 mL). The filtrate was evaporated under reduced pressure, the resulting residue was dissolved in THF (240 mL), piperidine (3.26 mL, 32.96 mmol) was added, and the mixture was stirred at reflux for 5 h. After cooling, the solution was concentrated to dryness, and the residual material was purified by column chromatography (eluent: 100% dichloromethane) to give 7-aminothieno[2,3-b]pyrazine-6-carbonitrile 1d as a yellow powder (3.66 g, 63%); Rf ? 0.18 (dichloromethane); mp 205e207 C (lit. [8b]: 205e 206 C); IR (KBr) nmax (cm 1): 3383, 3329, 3231 and 3204 (nNH2), 2197 (nCN), 1643, 1566 and 1529 (nC]C); 1H NMR (400 MHz, DMSO-d6): d 8.86 (d, 1H, J ? 2.4 Hz), 8.84 (d, 1H, J ? 2.4 Hz), 7.45 (br s, 2H, NH2); 13C NMR (100 MHz, DMSO-d6):d 154.55 (C), 149.15 (C), 145.26 (CH), 142.36 (CH), 139.76 (C), 115.37 (CN), 74.27 (C); MS (ESI) m/z (%): 177.0 (100) [M th H]th. Anal. Calcd for C7H4N4S: C, 47.72; H, 2.29; N, 31.80; S, 18.20. Found: C, 47.84; H,2.30; N, 31.86.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropyrazine-2-carbonitrile, its application will become more common.
Reference:
Article; Loidreau, Yvonnick; Marchand, Pascal; Dubouilh-Benard, Carole; Nourrisson, Marie-Renee; Duflos, Muriel; Lozach, Olivier; Loaec, Nadege; Meijer, Laurent; Besson, Thierry; European Journal of Medicinal Chemistry; vol. 58; (2012); p. 171 – 183;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem