5-IODOURIDINE

58-96-8

1024-99-3

The general procedure for the synthesis of 5-iodouridine from 1-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione was carried out as follows: in a round-bottomed flask, uracil (1 g, 4.1 mmol) and iodine (1.15 g, 4.5 mmol) were dissolved in a mixture of chloroform (55 ml) and 1M Nitric acid (10 ml) in a mixed solution. The reaction mixture was heated to 80°C and refluxed for 5 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and the unfolding agent was a chloroform solution of 30% methanol (Rf: 0.60; raw material Rf: 0.45). After completion of the reaction, the mixture was cooled to 4 °C and colorless needle-like 5-iodouridine crystals were precipitated. The precipitate was collected by filtration and dried under vacuum overnight to give 1.39 g of 5-iodouridine in 92% yield. The product was subjected to nuclear magnetic resonance hydrogen (1H NMR, DMSO-d6, 300 MHz) and carbon (13C NMR, DMSO-d6, 300 MHz) spectra to confirm the structure, and mass spectrometry (ESI) showed that the molecular ion peak [M+NH4]+ was 388.0000, which was consistent with the theoretical value.