Electric Literature of 14508-49-7,Some common heterocyclic compound, 14508-49-7, name is 2-Chloropyrazine, molecular formula is C4H3ClN2, 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.
b) 2 4-Methylpiperazin-1-yl)-/V-pyrazin-2-yl-2,4′-bipyridin-6-amine; An oven dried resealable Schlenk tube was charged with 2′-(4-methylpiperazin-1-yl)- 2,4′-bipyridin-6-amine (example 34a, 0.09 g, 0.33 mmol), 2-chloropyrazine (0.04 mu, 0.39 mmol), sodium terf-butoxide (0.04 g, 0.38 mmol) and dioxane (1 ml_). The Schlenk tube was subjected to three cycles of evacuation-backfilling with argon, and tris(dibenzylideneacetone)dipalladium(0) (0.01 g, catalytic amount) and 4,5- bis(diphenylphosphino)-9,9-dimethylxanthene (0.01 g, catalytic amount) were added. After three further cycles of evacuation-backfilling with argon, the Schlenk tube was capped and placed in an oil bath at 95 C. After 16h, the mixture was cooled and the solvent was removed in vacuo. The residue was purified by flash chromatography to give the title compound (0.09 g, 82%) as a solid.LRMS (m/z): 348 (M+1)+.1 H NMR (500 MHz, CHLOROFORM-d) delta ppm 2.35 (s, 3 H) 2.53 – 2.55 (m, 4 H) 3.63 – 3.66 (m, 4 H) 7.16 (dd, =6.50, 2 Hz, 1 H) 7.34 (s, 1 H) 7.39 (d, J=9.00 Hz, 1 H) 7.61 (d, J=10.00 Hz, 1 H) 7.73 (t, J=10.00 Hz, 1 H) 7.96 (br. s., 1 H) 8.13 (d, J=3.50 Hz, 1 H) 8.19 – 8.21 (m, 1 H) 8.13 (d, J=3.50 Hz, 1 H) 8.98 (d, J=2.00 Hz, 1 H)
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2-Chloropyrazine, its application will become more common.
Reference:
Patent; ALMIRALL, S.A.; VIDAL JUAN, Bernat; FORNS BERENGUEL, Maria Pilar; CASTILLO MCQUADE, Marcos; ERRA SOLA, Montserrat; MIR CEPEDA, Marta; WO2012/41476; (2012); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem