[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[CH:12][CH:11]=2)[CH:6]=[CH:5][N:4]=1.[N+:17]([O-])([OH:19])=[O:18].C([O-])(O)=O.[Na+]>CC(O)=O.O>[CH3:1][NH:2][C:3]1[N:8]=[C:7]([O:9][C:10]2[CH:15]=[CH:14][C:13]([OH:16])=[C:12]([N+:17]([O-:19])=[O:18])[CH:11]=2)[CH:6]=[CH:5][N:4]=14-(2-Methylamino-pyrimidin-4-yloxy)-phenol (Step C, 0.20 g, 0.92 mmol) was dissolved in 5 mL AcOH at RT. Fuming HNO3 (0.064 g, 0.92 mmol) was diluted with about 0.012 mL water, then added dropwise over 1 min to the reaction. The reaction was stirred for 18 h, after which it was added slowly to 40 mL saturated aqueous NaHCO3 and extracted with CH2Cl2. The organic layer was washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by silica gel column chromatography using hexanes/EtOAc gradient to yield the title compound. MS (MH+)=263.1; Calc'd 262.23 for C11H10N4O4.
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