Urea → HCID 20295827, compound

Participants

Reaction Steps

A mechanically stirred solution of urea (60.06 g, 1 mol) and dimethyl fluoromalonate (150.11 g, 1 mol) in methanol (1 L) was treated with 25 wt % NaOMe in methanol (˜4.6 M, 435 mL, 2 mol). The mixture was refluxed for 3 h and then allowed to cool to room temperature. The mixture was filtered, the wet cake was dissolved in warm water (˜1.2 L), and the resulting aqueous solution was acidified with concentrated aqueous HCl (˜160 mL) to pH=2 while stirring over 1 h. The mixture was allowed to cool to room temperature, and the product was filtered and washed thoroughly with water, then dried under vacuum to give 5-fluoro-6-hydroxy-2,4(1H,3H)-pyrimidinedione (80 g, 55%) as a white solid. LCMS: (M+H)+: 147.0.

Provenance & Evidence