Electric Literature of 3149-28-8, A common heterocyclic compound, 3149-28-8, name is 2-Methoxypyrazine, molecular formula is C5H6N2O, 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.
To a solution of lithium 2,2,6,6-tetra-methylpiperidide (2.6 mmol, 0.5 M in THF) at -78 C was added a solution of 2-methoxypyrazine (220 mg, 2.0 mmol) in THF (5 mL). The reaction mixture was stirred at -78 C for 30 min. Ethyl formate (167 mg, 0.18 mL, 2.3 mmol) was added and stirring was continued for 30 min at -78 C. A mixture of hydrochloric acid (35% aq, 1 mL), ethanol (1 mL) and THF (4 mL) was added and the resulting mixture was warmed to room temperature, neutralized with NaHCO3 (satd, 5 mL) and evaporated to near dryness. The residue was extracted with dichloromethane (3×25 mL). The organic extract is dried (MgSO4) and reduced in vacuo. The crude residue was purified by flash column chromatography using n-hexanes/ethyl acetate (3:1) as eluent to give the title compound as a yellow solid (193 mg, 1.4 mmol, 70%); mp 47-49 C (lit.10 mp 66-67 C); numax (neat)/cm-1 2955, 2797, 1710, 1534, 1468, 1365, 1305, 1072, 954, 762; deltaH (400 MHz, CDCl3) 10.27 (1H, s, CHO), 8.37 (1H, d, J 2.4, CH), 8.35 (1H, d, J 2.4, CH), 4.13 (3H, s, Me); deltaC (100 MHz, CDCl3) 190.1 (CHO), 160.5 (C), 145.7 (CH), 137.5 (CH), 136.3 (C), 54.5 (Me); m/z (ESI) 161 (100%, [M+Na]+); HRMS (ESI, [M+Na]+) found 161.0322. [C6H6N2NaO2]+ requires 161.0321.
The synthetic route of 3149-28-8 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Wang, Christy; Sperry, Jonathan; Tetrahedron; vol. 70; 21; (2014); p. 3430 – 3439;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem