[CH3:1]OC(OC)COC.[CH3:9][C:10]1([CH3:18])[O:15][C:14](=[O:16])[CH2:13][C:12](=[O:17])[O:11]1.[CH3:19][O:20][C:21]1[CH:22]=[C:23]([NH2:29])[CH:24]=[N:25][C:26]=1[O:27][CH3:28]>>[CH3:19][O:20][C:21]1[CH:22]=[C:23](/[N:29]=[CH:1]/[CH:13]2[C:14](=[O:16])[O:15][C:10]([CH3:18])([CH3:9])[O:11][C:12]2=[O:17])[CH:24]=[N:25][C:26]=1[O:27][CH3:28]A round bottom flask was charged with 2-methoxyacetaldehyde dimethyl acetal (2076 μl, 2076 μmol) and 2,2-dimethyl-1,3-dioxane-4,6-dione (299 mg, 2076 μmol). The flask was fitted with a reflux condenser and the mixture was heated at 100° C. for 2 h under nitrogen. 5,6-Dimethoxypyridin-3-amine (320 mg, 2076 μmol) was added, and within a minute a solid had precipitated out of solution. The heterogeneous mixture was heated at 100° C. for 10 min. The mixture was cooled to RT and the solids were filtered and washed with hexanes. (E)-5-((5,6-dimethoxypyridin-3-ylimino)methyl)-2,2-dimethyl-1,3-dioxane-4,6-dione was isolated as a yellow/orange solid. MS [M+H]=309.
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