反应详情

温度

100 °C

To 6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.05 g, 0.25 mmol) and 5-iodopyridin-2-amine (0.067 g, 0.304 mmol) in dioxane (1 ml) was added potassium phosphate (0.08 g, 0.377 mmol). The reaction mixture was degassed for 5 minutes and to this was added trans-diamino cyclohexane (0.004 g, 0.03 mmol) followed by copper (I) iodide (0.006 g, 0.03 mmol) and the mixture heated to 100° C. for 1 hour. Water was added and the product extracted with ethyl acetate (3×10 ml), dried over anhydrous sodium sulfate and concentrated. The product was further purified by reverse phase HPLC (C18) to yield pure 3-(6-aminopyridin-3-yl)-6-fluoro-7-(methylamino)-2,3-dihydrobenzo[e][1,3]oxazin-4-one (0.017 g, 23%). RP-HPLC: 1.5 min; ES-MS (M+H)+=289.1; 1H-NMR (MeOH-d4) δ (ppm): 2.82 (s, 3), 5.4 (s, 2), 6.2 (d, 1), 6.6 (d, 1), 7.3 (d, 1), 7.4 (dd, 1), 7.8 (s, 1).

1. customThe reaction mixture was degassed for 5 minutes
2. extractionthe product extracted with ethyl acetate (3×10 ml)
3. dry with materialdried over anhydrous sodium sulfate
4. concentrationconcentrated
5. customThe product was further purified by reverse phase HPLC (C18)