C([Li])CCC.C1COCC1.[CH3:11][NH:12][CH3:13].C1COCC1.Cl[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([OH:26])[CH:25]=1>C(O)C>[CH3:11][N:12]([CH3:13])[C:20]1[CH:21]=[N:22][CH:23]=[C:24]([OH:26])[CH:25]=1At −70° C., a 1.59 M normal-butyllithium/THF solution (14.6 ml) was added to s 2 M dimethylamine/THF solution (11.6 ml), followed by stirring for 10 minutes. This was warmed to 0° C., and 3-chloro-5-hydroxypyridine (1.00 g) was added thereto, followed by stirring overnight at room temperature. Ethanol (15 ml) was added, and the solvent was evaporated under reduced pressure. Water was added to the residue, followed by extraction with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v)) to obtain 3-dimethylamino-5-hydroxypyridine (176 mg).
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