反应详情

1N NaOH was added to a 50 mL pear flask charged with (S)-5-(1-((2,6-diamino-5-cyanopyrimidin-4-yl)amino)ethyl)-1-methyl-6-morpholino-1H-pyrrolo[3,2-b]pyridin-3-yl acetate (3.29 g, 7.29 mmol) in methanol (25 mL). The reaction was complete within about 15 minutes. Saturated sodium bicarbonate solution was added. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated. The crude product was purified by preparative HPLC (acid mode, 5% to 25% ACN/water gradient). The product-containing fractions were pooled, neutralized with saturated sodium bicarbonate, and then extracted with EtOAc (3×). The combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound as an off-white solid (210 mg, 7.04%). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.34 (d, J=6.57 Hz, 3 H), 2.70-2.80 (m, 2 H), 2.96-3.07 (m, 2 H), 3.15 (s, 3 H), 3.63 (d, J=2.53 Hz, 2 H), 3.71-3.88 (m, 4 H), 5.78-5.96 (m, 1 H), 6.07 (s, 1 H), 6.41 (br s, 2 H), 6.60 (s, 2 H), 7.33 (s, 1 H); ESI-MS m/z [M+H]+ calc'd for C19H23N9O2, 410; found 410.

1. extractionThe aqueous layer was extracted with EtOAc (3×)
2. dry with materialThe combined organic layers were dried over MgSO4
3. filtrationfiltered
4. concentrationconcentrated
5. customThe crude product was purified by preparative HPLC (acid mode, 5% to 25% ACN/water gradient)
6. extractionextracted with EtOAc (3×)
7. dry with materialThe combined organic layers were dried over MgSO4
8. filtrationfiltered
9. concentrationconcentrated