[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[CH2:12][C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2.[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>C1CCCCC1.[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([C:11]=1[C:12](=[CH2:19])[C:13]([O:15][CH3:16])=[O:14])=[N:9][C:8]([O:17][CH3:18])=[CH:7][CH:6]=2
To a solution of methyl [3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43 g, 162 mmol) in cyclohexane (1060 ml) was added benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g). The reaction mixture was then heated at 80° C. for 24 hours, cooled and treated with ethyl acetate and water. The aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed under reduced pressure. The residue was subjected to column chromatography on silica gel using a hexane and ethyl acetate gradient to provide the desired compound (40 g, 89%).
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