[CH:1]1([CH2:4][NH:5][C:6]2[C:11]([NH2:12])=[CH:10][CH:9]=[CH:8][N:7]=2)[CH2:3][CH2:2]1.C(NC(C)C)(C)C.Cl[C:21](=[O:27])[C:22](OCC)=[O:23].O>ClCCl>[CH:1]1([CH2:4][N:5]2[C:22](=[O:23])[C:21]([OH:27])=[N:12][C:11]3[CH:10]=[CH:9][CH:8]=[N:7][C:6]2=3)[CH2:2][CH2:3]1To 1.6 g (9.8 mM) of N2-(cyclopropylmethyl)pyridine-2,3-diamine and 1.7 ml (9.8 mM) of diisopropylamine in 20 ml of dichloromethane were added, drop by drop, under stirring; at room temperature, 1.1 ml (9.8 mM) of ethyl chloro(oxo)acetate. The reaction mixture was stirred at room temperature for 16 h and water was added. The organic layer was separated and the aqueous layer was extracted twice with dichloromethane. The combined organic layer was washed with water, dried on anhydrous sodium sulfate and the solvent was removed under vacuum. The compound was further purified by silica gel column chromatography using dichloromethane/methanol (95/5) as eluant, which afforded after evaporation 700 mg of 4-(cyclopropylmethyl)-2-hydroxypyrido[2,3-b]pyrazin-3(4H)-one as a solid. Yield: 33%.
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