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

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).

1. additionwere added
2. customa reaction at room temperature for 90 minutes
3. waitwas left
4. customThe reaction mixture was evaporated to dryness at reduced pressure
5. extractionthe residue was extracted in water-chloroform system
6. dry with materialAfter the chloroform layer was dried with anhydrous sodium sulfate, chloroform
7. distillationwas distilled away at reduced pressure
8. dissolutionThe residue was dissolved in 20 ml of dioxane
9. additionafter addition of aqueous ammonia
10. waitthe mixture was left
11. waitstanding at room temperature for 12 hours
12. concentrationIt was concentrated to dryness under reduced pressure
13. customThe residue was purified by C-18 reverse phase column chromatography on silica gel (20% acetone/water)

ORD record

ord-e2f8b603fc334ebabda010899ef76479

Source dataset

uspto-grants-1990_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04965350