反应详情

A mixture of 363 mg (0.9 mmol) of 1-(but-3-enyl)-N3-(2,6-dimethylphenyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine 33 (Example 1, Step D) and a catalytic amount of OsO4 in 28.5 mL acetone and 10 mL water was treated with 400 mg (97%, 3.3 mmol) of morpholine-N-oxide. The resulting yellow solution was stirred at room temperature for 18 h. The reaction mixture was diluted with water (95 mL) and extracted with CH2Cl2 (3×240 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4) to give the title compound. 1H-NMR (DMSO-d6) δ 1.58-1.69 (m, 1H), 1.91-2.01 (m, 1H), 2.20 (s, 6H), 3.19-3.27 (m, 1H), 3.28-3.36 (m, 1H), 3.88-3.97 (m, 1H), 4.05-4.19 (m, 2H), 4.48 (t, J=5.7 Hz, 1H), 4.56 (d, J=5.0 Hz, 1H), 6.94 (t, J=7.3 Hz, 1H), 7.05-7.14 (m, 3H), 7.27 (t, J=7.9 Hz, 2H), 7.85 (d, J=8.0 Hz, 2H), 8.08 (s, 1H), 8.36 (s, 1H), 9.65 (s, 1H). Mass Spectrum (ESI) m/e=419.2 (M+1).

1. extractionextracted with CH2Cl2 (3×240 mL)
2. dry with materialThe combined organic layers were dried over Na2SO4
3. filtrationfiltered
4. customthe filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4)