Reference of 89123-58-0, These common heterocyclic compound, 89123-58-0, name is 5-Bromopyrazine-2,3-diamine, 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.
5-Bromopyrazine-2,3-diamine (27) was preparedfrom 2-amino-3,5-dibromopyrazine and NH4OH (25%) in sealedtube according to lit.33 1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2),7.24 (s,2H,H-5,6). 13C-NMR (CD3OD): 123.3, 129.8, 144.3, 145.9. MS(ESI+) m/z: 189(M + H, 100%), 191(M + H+2, 97%). 27 (0.303 g,1.6 mmol) in EtOH (10 mL) was reduced by hydrogenation using 40psi of H2 and 10% Pd-C (15 mg) for 8 h. The catalyst was filtered ona bed of Celite, the filtrate was concentrated in vacuo. Purplecolored powder 28 were used for the further steps without purification.1H-NMR delta ppm (CD3OD): 4.90 (s,4H,NH2), 7.24 (s,2H, H-5,6). 13C-NMR (CD3OD): 123.7, 145.1. MS (ESI) m/z: 110(M + H,100%). 29 was prepared from 28 (0.11 g) and Na2S2O5 adduct of 4-(morpholin-4-ylcarbonyl) benzaldehyde (0.323 g) as described ingeneral method. Resulting precipitate (0.155 g) was purified withcolumn chromatography using CH2Cl2: MeOH (95 : 5) as eluant,yield 0.056 g, (18%), mp > 300 C. 1H-NMR delta ppm (DMSO-d6+D2O):3.27-3.61 (m,8H), 7.62 (d,2H,J – 8.4 Hz), 8.33 (d,2H,J – 8.4 Hz), 8.40(s,2H,H-5,6). 13C-NMR (DMSO-d6+D2O): 66.0, 127.3, 127.8, 129.9,138.2, 139.0, 154.7, 168.2. MS (ESI) m/z: 310(M + H, 100%). AnalCalcd for C16H15N5O2H2O: C, 58.70; H, 5.23; N, 21.39. Found: C,58.97; H, 5.01; N, 20.91.
Statistics shows that 5-Bromopyrazine-2,3-diamine is playing an increasingly important role. we look forward to future research findings about 89123-58-0.
Reference:
Article; Karaaslan, Cigdem; Doganc, Fatima; Alp, Mehmet; Koc, Asli; Karabay, Arzu Zeynep; Goeker, Hakan; Journal of Molecular Structure; vol. 1205; (2020);,
Pyrazine – Wikipedia,
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