Uses
2-Methylaminopyrazine is an N-methylated primary amine. 2-Methylaminopyrazine is an important class of organic synthetic reactions, widely used in the synthesis of natural products, fine chemicals, pharmaceuticals, and key intermediates. Early on, pyrazine compounds were mainly used as anti-tuberculosis, pinworm, anticonvulsant, and antibacterial agents. Since the detection of methylpyrazine, 2,5-dimethylpyrazine, and 2,6-dimethylpyrazine in coffee in 1928, nearly a hundred pyrazine compounds have been detected in many natural foods. Today, pyrazine compounds are widely used in the flavoring industry.
Synthesis
Report I.
Aminopyrazine (42 mg, 0.5 mmol), cat1 (3.2 mg, 0.005 mmol, 1 mol%), cesium carbonate (49 mg, 0.15 mmol, 0.3 equiv.), and methanol (1 mL) were added sequentially to a 25 mL Krebs tube. After reacting at a temperature of 120C for 12 hours, it was cooled to room temperature. The solvent was removed by rotary evaporation and the pure target compound was obtained by column chromatography (unfolding agent: petroleum ether/ethyl acetate), yield: 95%;
Report II.
The reaction was carried out by combining 2-aminopyrazine (190 mg, 2 mmol), [Cp*IrCl2]2 (1.6 mg, 0.002 mmol, 0.1 mol%), sodium hydroxide (80 mg, 2 mmol) and methanol (1 ml, 790 mg, 24.7 mmol, 12.4 equiv.) were added sequentially to a 20 ml Schlenk reaction flask. The reaction mixture was allowed to react at 150 oC for 12 hours and then cooled to room temperature. The solvent was removed by rotary evaporation and the target compound was obtained in pure form by column chromatography (developer: ethyl acetate/petroleum ether) in 90% yield.
