[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][N:8]([CH3:25])[CH2:9][CH2:10][NH:11][C:12]1[N:22]=[C:21]([CH3:23])[CH:20]=[C:19]([CH3:24])[C:13]=1[C:14](OCC)=[O:15]>O1CCCC1>[CH3:7][N:8]([CH3:25])[CH2:9][CH2:10][NH:11][C:12]1[C:13]([CH2:14][OH:15])=[C:19]([CH3:24])[CH:20]=[C:21]([CH3:23])[N:22]=1To a suspension of lithium aluminum hydride (3.5 g, 92 mmol) in dry tetrahydrofuran (160 ml) is added dropwise a solution of crude ethyl 2-(2-dimethylaminoethylamino)-4,6-dimethylnicotinate (18.5 g, 70 mmol) in dry tetrahydrofuran (100 ml) under a nitrogen atmosphere. Reaction mixture is refluxed for 11/2 hours, cooled, quenched with saturated sodium sulfate solution filtered, dried and evaporated to give 15.0 g of crude title C product.
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