[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[CH3:12][O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1A mixture of methyl 3-hydroxypyridine-2-carboxylate (Intermediate 96, 1.2 g, 7.8 mmol), potassium carbonate (1.2 g, 8.7 mmol), iodomethane (0.63 ml, 1.0 mmol) and DMF (10 ml) was stirred overnight. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water and concentrated under vacuum. The residue (0.82 g) was purified by flash column chromatography (5 g silica; heptane-ethyl acetate, 1:0-5:1-2:1) to give the title compound as a clear oil (0.58 g, 45%). Method C HPLC-MS: MH+ requires m/z=168. Found: m/z=168, Rt=0.76 min (100%).
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