[C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][C:13](=O)[NH:14][C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[C:1]1([C:7]2[CH:17]=[N:16][C:10]3[O:11][CH2:12][CH2:13][NH:14][C:9]=3[CH:8]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
7-phenyl-1H-pyrido[2,3-b][1,4]oxazin-2-one (21 mg, 0.09 mmol) was dissolved in tetrahydrofuran (0.5 ml) and then cooled to 0□. 1.0M Lithium aluminum hydride dissolved in tetrahydrofuran (0.19 ml, 0.19 mmol) was added thereto dropwise. After stirring for 5 hours at room temperature, 0.1 ml of water, 0.2 ml of 10% aqueous solution of sodium hydroxide, and 0.3 ml of water were added in this order under stirring. After filtering precipitates, the filtrate was extracted with ethyl acetate. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of dichloromethane:methanol=40:1. The fractions containing the product were collected and evaporated to obtain pale-grey solid (10 mg, 50%).
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