Reaktion #1435754

Reaktionsgleichung

uridine

diphenyl carbonate

hexamethylphosphoric triamide

→

title compound 15

Ausbeute 84.0%

1-(β-D-Arabinofuranosyl)uracil

Ausbeute 84.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturcooled to room temperature
3. 3
   Waschenwashed with CHCl3
4. 4
   workup.ADDITIONEt3N (25 mL) was added
5. 5
   Temperaturthe aqueous solution was heated at 70° C. for 5 h
6. 6
   SonstigeThe solvent was evaporated in vacuo
7. 7
   Sonstigethe residue was crystallized from MeOH/water

Vorschrift

A mixture of uridine (14; 13.25 g, 54.5 mmol), diphenyl carbonate (15.48 g, 72.5 mmol), anhydrous NaHCO3 (349 mg, 4.15 mmol), and hexamethylphosphoric triamide (50 mL) was heated with stirring at 150° C. under nitrogen for 20 min, and then cooled to room temperature. The mixture was poured into cold water (400 mL), and washed with CHCl3. Et3N (25 mL) was added, and the aqueous solution was heated at 70° C. for 5 h. The solvent was evaporated in vacuo, and the residue was crystallized from MeOH/water to give the title compound 15 as a white solid (11.13 g, 84%). 1H NMR (DMSO-d6) δ 11.2 (s, 1H, NH), 7.60 (d, J=7.5 Hz, 1H, H-6), 5.95 (d, 1H, H-1′), 5.51 (d, J=7.5 Hz, 1H, H-5), 6.30–5.30 (br, 2H, 2 OH), 4.10–3.50 (m, 6H, H-2′, H-3′, H-4′, H-5′, OH).

Quelle