N-Alkylation and O-Alkylation of Ethyl 4-(4,6-Dimethoxypyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate

Twenty novel N-substitued and O-substitued compounds were prepared starting from ethyl 4-(4,6-dimethoxypyrimidin-2-yl)-2-oxo-1,2-dihydroquinoline-3-carboxylate. Various halogenated hydrocarbons were used as resource of alkylation and NaH as base in N,N-dimethylformamide (DMF) at room temperature. The structures of alkylation products were confirmed by H-1 NMR, IR, MS and elemental analysis. Two isomer structures were further determined by representative X-ray structures of N10 and 010. The alkylation reaction was performed in mild conditions with a total yield of 89%similar to 98%. Among them, the main product N-alkylation was obtained in 47%similar to 77% yield, and O-alkylation was simultaneously obtained in 21%similar to 49% yield by a simple one-pot reaction.