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Pre Step A 6-(Methyloxy)-2-pyrazinamine A mixture of 6-chloro-2-pyrazinamine (200 mg, 1.544 mmol) and sodium methoxide (250 mg, 4.63 mmol) in methanol (3.9 ml) was heated to 130° C. via a microwave reactor for 60 min. The crude product mixture was purified by RP-HPLC to give 6-(methyloxy)-2-pyrazinamine (154 mg, 1.231 mmol, 80percent yield). MS (ES+) m/z 125.8 (MH+).
11%
In 1,4-dioxane; methanol; ethyl acetate;
Step 1: 2-amino-6-methoxypyrazine. To a stirred solution of methanol (89 muL; 2.2 mmol) in dioxane (1 mL) was added sodium hydride (53 mg; 2.2 mmol). After stirring for 30 minutes, <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (258 mg; 2.0 mmol) was added and the reaction was heated to 90° C. After stirring for 12 hours, the reaction was cooled to room temperature, diluted with 30 mL of ethyl acetate and washed with aqueous 10percent sodium carbonate (1*30 mL), and brine (30 mL), then dried (MgSO4), and filtered. The crude product was purified using the Biotage 12i cartridge eluding with hexane and ethyl acetate (3:1) to yield a white solid (11percent yield).
To a mixture of MeOH (6 mL) in DMSO (12 mL) was added slowly NaH (1.2 g of 60percent in oil, 30 mmol) and stirred at room temperature for 30 min. <strong>[33332-28-4]2-amino-6-chloropyrazine</strong> (1.29 g, 10 mmol) was added to the mixture portionwise and heated at 80 °C for 2 h. The reaction mixture was cooled, water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified bycolumn chromatography to give 2-amino-6-methoxypyrazine (888 mg, 71percent) as a slightly yellow solid. 1H NMR (200 MHz, CDCl3) delta 7.60 (s, 1H), 7.55 (s, 1H), 4.44 (br, 2H), 3.90 (s, 3H); 2-amino-6-methoxyprazine (186 mg, 1.45 mmol) was dissolved in MeOH. To the solution was added N-bromo-succinimide (568 mg, 3.19 mmol) and stirred at room temperature for 30 min. The reaction mixture was concentrated via vacuo, ethyl acetate was added and washed with water. The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography to give a product 1e (242 mg, 59percent). 1H NMR (200 MHz, CDCl3) delta4.91 (br, 2H), 3.96 (s, 3H);
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