Extended knowledge of 2-Bromo-5H-pyrrolo[2,3-b]pyrazine

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference of 875781-43-4, A common heterocyclic compound, 875781-43-4, name is 2-Bromo-5H-pyrrolo[2,3-b]pyrazine, molecular formula is C6H4BrN3, 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 commercially available 2-bromo-5H-pyrrolo[2,3-b]pyrazine (1.00 g, 5.05 mmol) in N,N-dimethylformamide (10 mL) was added Cs2C03 (2.50 g, 7.67 mmol) and [2-(chloromethoxy)ethyl]trimethylsilane (1.26 g, 7.55 mmol). The reaction mixture was stirred overnight at room temperature and concentrated under vacuum. The residue was purified by flash chromatography on silica gel (solvent: 1/10 ethyl acetate/petroleum ether). Appropriate fractions were combined and evaporated to afford 2-bromo-5-[[2-(trimethylsilyl)ethoxy]methyl]-5H-pyrrolo[2,3-b]pyrazine (1.50 g, 90%) as a yellow solid. LC/MS (Method D, ESI): [M+H]+ = 328.0, RT = 1.23 min.

The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; F. HOFFMANN-LA ROCHE AG; GENENTECH, INC.; ZAK, Mark; ROMERO, F. Anthony; YUEN, Po-wai; HANAN, Emily J.; (139 pag.)WO2018/166993; (2018); A2;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem