[H-].[Al+3].[Li+].[H-].[H-].[H-].[NH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15](OC)=[O:16])=[CH:10][N:9]=1.O.[OH-].[Na+]>O1CCCC1>[NH2:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([CH2:15][OH:16])=[CH:10][N:9]=1To a mixture of lithium aluminum hydride (LAH) (90 mg, 2.37 mmol) in dry tetrahydrofuran (THF) (2 mL) was added a solution of 2-amino-5-methoxycarbonyl-4-methylpyridine (100 mg, 0.602 mmol) in THF (1 mL). The reaction mixture was stirred for 1 h at reflux temperature. Excess LAH was decomposed by successive addition of water (90 uL), 15% sodium hydroxide (90 uL), and water (270 uL). Solids were removed by filtration through a pad of Celite. The title compound was obtained as a white crystalline solid after chromatography on silica gel (5-15% methanol/methylene chloride).
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