Dimethylformamide → (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde

Participants

Reaction Conditions

Reaction Steps

To a solution of DMF (114.9 g, 1.57 mol) in CHCl3 (800 mL) was added dropwise oxalyl chloride (190.3 g, 1.50 mol) at 0° C. After the addition, the resulting mixture was warmed at 30° C. and stirred for 1 h. The mixture was allowed to cool to 0° C. and 4-methyl-2-(methylthio)pyrimidine (2) (100 g, 0.714 mol) was added to the mixture. The resulting mixture was warmed to 40° C. and stirred for 16 h. The reaction mixture was cooled to room temperature and filtered. The cake was washed with CHCl3 (150 mL×3) and dried in vacuum to give (E)-3-hydroxy-2-(2-(methylthio)pyrimidin-4-yl)acrylaldehyde (3) (342.0 g, 100%) as a yellow solid.

Provenance & Evidence