Реакция #1435754

Уравнение реакции

uridine

diphenyl carbonate

hexamethylphosphoric triamide

→

title compound 15

Выход 84.0%

1-(β-D-Arabinofuranosyl)uracil

Выход 84.0%

Растворители

water

Условия реакции

Обработка

1. 1
   Температураwas heated
2. 2
   Температураcooled to room temperature
3. 3
   Промывкаwashed with CHCl3
4. 4
   workup.ADDITIONEt3N (25 mL) was added
5. 5
   Температураthe aqueous solution was heated at 70° C. for 5 h
6. 6
   ДругоеThe solvent was evaporated in vacuo
7. 7
   Другоеthe residue was crystallized from MeOH/water

Методика

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).

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