[CH3:1][O:2][C:3](=[O:18])[CH2:4][C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([O:15][CH3:16])[N:13]=2)[N:8]=[CH:7][C:6]=1[Cl:17].[C:19](=O)([O-])[O-].[K+].[K+].C=O.C(OCC)(=O)C>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C1CCCCC1.O>[Cl:17][C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:5]=1[C:4](=[CH2:19])[C:3]([O:2][CH3:1])=[O:18])=[N:13][C:12]([O:15][CH3:16])=[CH:11][CH:10]=2A mixture of methyl[3-chloro-6-(methyloxy)-1,5-naphthyridin-4-yl]acetate (43.3 g, 162 mmol), benzyltriethylammonium chloride (71.2 g, 313 mmol), potassium carbonate (42 g, 304 mmol) and paraformaldehyde (42 g) in cyclohexane (1060 ml) was heated at 80° C. for 24 h, cooled and treated with ethyl acetate and water. After separation, the aqueous was extracted with ethyl acetate. The combined organic phases were dried and the solvent was removed. The residue was subjected to column chromatography on silica gel using hexane/15% ethyl acetate to provide the desired compound (40.2 g, 89%).
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