1,4-Dioxane → 2-Pyridinecarboxaldehyde, 3-[(4,6-dimethoxy-2-pyrimidinyl)oxy]-

Participants

Reaction Conditions

Reaction Steps

To a mixture consisting of 400 ml of dioxane and 400 ml of water, 42.6 g of 3-(4,6-dimethoxy-2-pyrimidinyloxy)-2-pyridinecarboxaldehyde diethylacetal and 22 g of N-hydroxybenzenesulfonamide were added under stirring. The reaction mixture was heated at 80-85° C. for 1 hour so that the reaction was brought to completion. Low-boiling substances were then distilled completion. Low-boiling substances were then distilled out under reduced pressure. The residue was added and extracted with 300 ml of saline and 300 ml of ethyl acetate. The organic layer was dried over sodium sulfate and then concentrated under reduced pressure, whereby 56.6 g of an oily residue was obtained. The residue was purified by chromatography on a silica gel column (n-hexane/ethyl acetate=1:1) so that 19.2 g of 4,6-dimethoxy-2-(2-formyl-3-pyridyloxy)pyrimidine were obtained (yield: 54%).

Provenance & Evidence