[C:1]1([CH2:7][O:8][C:9]2[N:14]=[CH:13][C:12]([NH2:15])=[CH:11][CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CC=CC=1.[CH3:22][C:23](OC(C)=O)=[O:24].O>C(Cl)Cl.CN(C1C=CN=CC=1)C>[C:1]1([CH2:7][O:8][C:9]2[N:14]=[CH:13][C:12]([NH:15][C:23](=[O:24])[CH3:22])=[CH:11][CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
To a solution of 6-[(phenylmethyl)oxy]-3-pyridinamine (0.213 g, 1.07 mmol; step B above) in CH2Cl2 (5 mL) at rt was added pyridine (0.17 mL, 2.14 mmol), DMAP (0.0065 g, 0.050 mmol) and Ac2O (0.12 mL, 1.28 mmol). After 5 min the mixture was poured into water and extracted with CH2Cl2 (×3). The combined organics were washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (EtOAc/hexanes), affording 0.245 g of the title compound as a colorless solid: MS (ESI) m/z 243 (M+1).
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