反应详情

To a solution of 23 mg (0.13 mmol) of 4,6-diamino-2-propyl-nicotinonitrile (Example 68B) and 50 mg (0.63 mmol) of pyridine in 1 mL of CH2Cl2 was added 35 mg (0.16 mmol) of (2,5-dimethoxyphenyl)acetyl chloride (Example 68A). The mixture was stirred at ambient temperature for 10 minutes then diluted with 3 mL of water. The mixture was extracted with ethyl acetate (3×3 mL), then the combined ethyl acetate layers were back extracted with saturated NaHCO3(aq.) (1×3 mL), and brine (1×3 mL), dried over MgSO4, filtered, and concentrated to an oil. This was suspended in 5 mL of toluene, then concentrated under reduced pressure to remove some pyridine. The product was purified via silica gel chromatography, eluting with 60:40 ethyl acetate:hexanes to provide 21 mg (46%) of a white solid. 1H NMR (300 MHz, d6-DMSO) δ 10.27 (s, 1H), 7.34 (s, 1H), 6.83 (m, 5H), 3.70 (m, 6H), 3.65 (s, 2H), 2.64 (m, 2H), 1.68 (m, 2H), 0.93 (t, 3H, J=7.3 Hz); MS (ESI) m/e 355 (M+H)+, 353 (M−H)−.

1. extractionThe mixture was extracted with ethyl acetate (3×3 mL)
2. extractionthe combined ethyl acetate layers were back extracted with saturated NaHCO3(aq.) (1×3 mL), and brine (1×3 mL)
3. dry with materialdried over MgSO4
4. filtrationfiltered
5. concentrationconcentrated to an oil
6. concentrationconcentrated under reduced pressure
7. customto remove some pyridine
8. customThe product was purified via silica gel chromatography
9. washeluting with 60:40 ethyl acetate