Water → 5-(2-cyanovinyl)-2'-deoxyuridine

Participants

Reaction Steps

2.00 g of 3', 5'-di-O-acetyl-(E)-5-(2-cyano-ethenyl) deoxyuridine (c) was dissolved in 20 ml of absolute acetonitrile, to which 9.2 ml of triethylamine, 1.12 ml of phosphorus oxychloride, and further 50 ml of 1.3 M triazole acetonitrile solution were added. The mixture was allowed to undergo a reaction at room temperature for 90 minutes. Water was added to the reaction mixture and it was left standing for 10 minutes. The reaction mixture was evaporated to dryness at reduced pressure and the residue was extracted in water-chloroform system. After the chloroform layer was dried with anhydrous sodium sulfate, chloroform was distilled away at reduced pressure. The residue was dissolved in 20 ml of dioxane, and after addition of aqueous ammonia, the mixture was left standing at room temperature for 12 hours. It was concentrated to dryness under reduced pressure. The residue was purified by C-18 reverse phase column chromatography on silica gel (20% acetone/water) to give 1.28 g of (E)-5-(2-cyanoethenyl) deoxyuridine (e).

Provenance & Evidence