These common heterocyclic compound, 4858-85-9, name is 2,3-Dichloropyrazine, 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. 4858-85-9
To a flame dried 25 mL flask with zinc dust (217 mg, 3.31 mmol) and N,N-dimethylacetamide (2 mL) was added chlorotrimethylsilane (33.5 muL, 0.265 mmol) and 1,2- dibromoethane (22.83 muL, 0.265 mmol). The resulting slurry was stirred 15 min, then tert-butyl 3-iodoazetidine-l-carboxylate (753 mg, 2 66 mmol) was added to the above mixture (mild exotherm). The suspension was stirred at rt 30 min. [00422] The zinc solution was added via syringe to a solution of 2,3-dichloropyrazine (277 mg, 1.862 mmol), (dppf)PdCl2-CH2Cl2 (65.2 mg, 0.080 mmol), and copper(I) iodide (30.4 mg, 0.160 mmol) in N,N-dimethylacetamide (1.0 mL) that was degassed with N2 (3 x). The solution was heated to 80 0C and stirred 1 h. The reaction was quenched with NH4Cl (10 mL) and extracted with EtOAc (3 x 10 mL). The combined organic fractions were dried (MgSO4), concentrated, and purified by ISCO (40 g SiO2, 10-100% EtOAc/Hexane) to give tert-butyl 3-(3- chloropyrazin-2-yl)azetidine-l-carboxylate (262 mg, 0.971 mmol, 36.5 % yield) as a clear, colorless oil.
Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 4858-85-9.
Reference:
Patent; AMGEN INC.; ALLEN, Jennifer R.; BOURBEAU, Matthew P.; CHEN, Ning; HU, Essa; KUNZ, Roxanne; RUMFELT, Shannon; WO2010/57121; (2010); A1;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem