[NH2:1][C:2]1[N:7]=[C:6]([C:8](OC)=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[Cl-].[Ca+2].[Cl-].[BH4-].[Na+].Cl.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.C(O)C>[NH2:1][C:2]1[C:3]([C:12]([O:14][CH3:15])=[O:13])=[CH:4][CH:5]=[C:6]([CH2:8][OH:9])[N:7]=1Dimethyl 6-aminopyridine-2,5-dicarboxylate (395 mg) was suspended in a mixed solvent (16 ml) of tetrahydrofuran/ethanol (1/1), calcium chloride (834 mg) and sodium borohydride (85.5 mg) were added thereto under ice-cooling, and the mixture was stirred for 2 hr. The reaction mixture was acidified with 1M hydrochloric acid, basified with saturated aqueous potassium carbonate solution, and extracted with ethyl acetate. The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure to give the title compound (296 mg) as a white solid.
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