Electric Literature of 6863-73-6,Some common heterocyclic compound, 6863-73-6, name is 3-Chloropyrazin-2-amine, molecular formula is C4H4ClN3, 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 3-Chloro-2-nitropyrazine STR11 Step A: S,S-Dimethyl-N-(3-chloropyrazin-2-yl)sulfilimine (2) To a mechanically stirred solution of 3.9 g (0.05 mol) dimethyl sulfoxide in 30 ml dry methylene chloride at -78 under nitrogen is added 13.1 g (0.046 mol) trifluoromethanesulfonic anhydride dropwise to afford a white precipitate. To this is added a solution of 5.0 g (0.039 mol) 2-amino-3-chloropyrazine (1) in 30 ml methylene chloride/15 ml dimethyl sulfoxide and the resulting solution is stirred at -78 for 2 hours and at -55 for 1 hour. The reaction mixture is then quenched with 50 ml of 5% aqueous sodium bicarbonate solution and stirred at -5 for 5 minutes. The reaction mixture is diluted with 200 ml methylene chloride and the phases are separated. The aqueous phase is extracted with 250 ml methylene chloride and the combined organic phases are washed with 3*75 ml portions of water and dried over anhydrous sodium sulfate. The solvent is removed from the rotary evaporator to give 5.8 g (79%) of 2 as yellow crystals, m.p. 106-108.
These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 3-Chloropyrazin-2-amine, its application will become more common.
Reference:
Patent; Merck & Co., Inc.; US4709035; (1987); A;,
Pyrazine – Wikipedia,
Pyrazine | C4H4N2 – PubChem