109-08-0, name is 2-Methylpyrazine, belongs to Pyrazines compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. 109-08-0
Compound 16: (E)-2-[2-(Pyridin-2-yl)vinyl]pyrazine hydrochloride: s-Butyl lithium (2.5 M in hexanes, 4.8 mL, 12.0 mmol, 1.2 eq.) was added dropwise to a solution of diisopropylamine (1.83 mL, 1.32 g, 13.0 mmol, 1.3 eq.) in dry tetrahydrofuran (25 mL) at -78 ¡ãC. The mixture was stirred at -78 ¡ãC for 10 min and 2-methylpyrazine (0.91 mL, 0.94 g, 10.0 mmol, 1.0 eq.) was added dropwise. The resulting mixture was stirred at -78 ¡ãC for a further 30 min. 2-Pyridinecarboxaldehyde (0.96 mL, 1.07 g, 10.0 mmol, 1.0 eq.) was added dropwise and the mixture was allowed to slowly warm up to room temperature over 1 h while stirring. The reaction was quenched by addition of water (10 mL). The pH was adjusted to -10 by careful addition of cone. HCl and then the mixture was extracted with dichloromethane (2 x 25 mL). The combined organic extracts were washed with brine (25 mL), dried over sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (Si02, 1:9 methanol-ethyl acetate) to provide 2-(pyrazin-2-yl)-1-(pyridin-2-yl)ethanol (1.08 g, 54percent yield) as a clear yellow oil. p-Toluenesulfonyl chloride (1.12 g, 5.9 mmol, 1.1 eq.) was added to a stirred solution of 2- (pyrazin-2-yl)-1-(pyridin-2-yl)ethanol (1.08 g, 5.4 mmol, 1.0 eq.) and triethylamine (2.24 mL, 1.63 g, 16.1 mmol, 3.0 eq.) in dichloromethane (25 mL). The mixture was stirred at room temperature for 23 h. The mixture was washed with aqueous NaOH (15percent, 25 mL), water (25 mL) and brine (25 mL). The organic layer was dried over sodium sulfate and evaporated in vacuo. The crude product was purified by column chromatography (Si02, 1:9 methanol-ethyl acetate) providing a mixture of 2-(pyrazin-2-yl)-1-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate and (E)-2-(2-(pyridin-2-yl)vinyl)pyrazine (0.54 g). l,8-Diazabicyclo[5.4.0]undec-7-ene (0.45 mL, 0.46 g, 3.0 mmol, 2.0 eq.) was added dropwise to a stirred solution of 2-(pyrazin-2-yl)-1-(pyridin-2-yl)ethyl 4-methylbenzenesulfonate (0.54 g, 1.5 mmol, 1.0 eq.) in dichloromethane (10 mL). The mixture was stirred at room temperature for 4 h. The mixture was evaporated in vacuo and the crude product was purified by column chromatography (SiO2, ethyl acetate) providing (E)-2-(2-(pyridin-2-yl)vinyl)pyrazine (0.50 g, 100percent) as a white solid. A solution of hydrochloric acid (2.0 M in diethyl ether, 0.65 mL, 1.3 mmol, 1.2 eq.) was added dropwise to a stirred suspension of (E)-2-(2-(pyridin-2-yl)vinyl)pyrazine (0.20 g, 1.1 mmol, 1.0 eq.) in dry diethyl ether (7.5 mL). The mixture was stirred at room temperature for 1 h and then the solids removed by filtration. The product was washed with diethyl ether (3 x 10 mL) and then dried in vacuo to provide (E)-2-[2-(pyridin-2-yl)vinyl]pyrazine hydrochloride (0.21 g, 83percent yield) as a fine white solid; 1H NMR (400 MHz, DMSO-d6) delta 7.78 (t, J = 7.0 Hz, 1H, Ar), 7.99 (d, J = 16.0 Hz, 1H, C=CH), 8.11 (d, J = 16.0 Hz, 1H, C=CH), 8.25 (d, J = 8.0 Hz, 1H, Ar), 8.38 (t, J = 8.0 Hz, 1H, Ar), 8.65 (d, J = 2.5 Hz, 1H, Ar), 8.75 (t, J = 2.0 Hz, 1H, Ar), 8.79 (d, J = 5.0 Hz, 1H, Ar), 8.88 (d, J = 2.0 Hz, 1H, Ar).
Statistics shows that 109-08-0 is playing an increasingly important role. we look forward to future research findings about 2-Methylpyrazine.
Reference:
Patent; UNIVERSITY COLLEGE DUBLIN – NATIONAL UNIVERSITY OF IRELAND, DUBLIN; THE PROVOST, FELLOWS, FOUNDATION SCHOLARS, AND THE OTHER MEMBERS OF BOARD, OF THE COLLEGE OF THE HOLY AND UNDIVIDED TRINITY OF QUEEN ELIZABETH, NEAR DUBLIN; KENNEDY, Breandan; REYNOLDS, Alison; O’SULLIVAN, Jacintha; BAXTER, Andrew, Douglas; WO2015/107122; (2015); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem