Electric Literature of 59489-71-3,Some common heterocyclic compound, 59489-71-3, name is 2-Amino-5-bromopyrazine, molecular formula is C4H4BrN3, 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.
Example 1; iV-(2-(4-(isopropylsulfonyl)phenyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl)benza mide (Compound 1-1)METHOD A:Step 1: 5-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine[00187] 5-Bromopyrazin-2-amine (5 g, 28.74 mmol), (4-isopropylsulfonylphenyl) boronic acid (7.866 g, 34.49 mmol) and K3P04 (12.20 g, 57.48 mmol) were combined in MeCN (100 mL) / Water (25 mL) and Pd[P(tBu)3]2 (734.4 mg, 1.437 mmol) was added. The reaction was heated at 60 C for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (x 3). The combined organic layers were dried (MgS04), filtered andconcentrated in vacuo. The residue was triturated from DCM and isolated by filtration to give the sub-title compound as an orange solid (6.43 g, 76% Yield). ¾ NMR (400.0MHz, DMSO) delta 1.17 (d, 6H), 3.43 (sept, IH), 6.86 (s, 2H), 7.87 (d, 2H), 8.00 (s, IH), 8.20 (d, 2H) and 8.67 (s, IH) ppm; MS (ES+) 278.2.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Amino-5-bromopyrazine, its application will become more common.
Reference:
Patent; VERTEX PHARMACEUTICALS INCORPORATED; MACCORMICK, Somhairle; STORCK, Pierre-henri; MORTIMORE, Michael, Paul; CHARRIER, Jean-damien; KNEGTEL, Ronald; YOUNG, Stephen, Clinton; PINDER, Joanne; DURRANT, Steven, John; WO2012/178123; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem