Synthetic Route of 113305-94-5, These common heterocyclic compound, 113305-94-5, name is 5-Aminopyrazine-2-carbonitrile, 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.
A solution of tert-butyl 4-((2-chloro-5-iodopyridin-4-ylamino)methyl)piperidine-1- carboxyiate (Synthesis 170-B) (0.100 g, 0.22 mmol), dichlorobis(triphenyiphosphine)- palladium (II) (0.009 g, 0.01 mmol), trimethyl(2-methylbut-3-yn-2-yloxy)silane (0.048 mL, 0.24 mmol) and copper iodide (0.002 g, 0.01 mmol) was heated under microwave irradiation for 5 min at 120 0C. The crude mixture was concentrated in vacuo and filtered through a pad of silica, eluting with hexane / ethyl acetate (8 / 2), to give the crude product which was used without further purification. The crude pyridine (0.085 g, 0.163 mmol), 2-amino-4-cyanopyrazine (0.023 g, 0.195 mmol), Xantphos (0.015 g, 0.026 mmol), cesium carbonate (0.106 g, 0.326 mmol), dichlorobis(triphenylphosphine)- palladium (II) (0.012 g, 0.013 mmol) in dioxane (1.2 mL) were stirred at room temperature under nitrogen for 10 min, then heated under microwave irradiation for 60 min at 150 CC. The reaction mixture was purified by ion exchange on SCX-II acidic resin (2 g), eluting with methanol / dichloromethane (1 / 1 ), then 2M ammonia-methanol. The basic fractions were combined and solvent was removed in vacuo. The crude product was purified by preparative thin layer chromatography, eluting with methanol / dichloromethane (1 / 19), to give the title compound as a yellow solid (0.024 g, 27%).1H NMR (CDCI3, 500 MHz) delta 8.62 (s, 1 H), 8.44 (s, 1 H), 8.00 (s, 1 H), 7.17 (s, 1 H), 5.19 (t, 1 H, J = 5.8 Hz) 4.19-4.16 (m, 2H), 3.17 (t, 2H, J = 6.1 Hz), 2.72 (t, 2H, J = 11.3 Hz), 1.84- 1.75 (m, 3H), 1.66 (s, 6H), 1.47 (s, 9H), 1.27-1.21 (m, 2H), 0.90-0.84 (m, 1 H). LCMS (4) Rt = 2.17 min; m/z (ESI+) 492 [MH+].
Statistics shows that 5-Aminopyrazine-2-carbonitrile is playing an increasingly important role. we look forward to future research findings about 113305-94-5.
Reference:
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; WO2009/44162; (2009); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem