تفاعل #1435754

معادلة التفاعل

uridine

diphenyl carbonate

hexamethylphosphoric triamide

→

title compound 15

المردود 84.0%

1-(β-D-Arabinofuranosyl)uracil

المردود 84.0%

المذيبات

water

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas heated
2. 2
   درجة الحرارةcooled to room temperature
3. 3
   غسيلwashed with CHCl3
4. 4
   workup.ADDITIONEt3N (25 mL) was added
5. 5
   درجة الحرارةthe aqueous solution was heated at 70° C. for 5 h
6. 6
   أخرىThe solvent was evaporated in vacuo
7. 7
   أخرىthe residue was crystallized from MeOH/water

الإجراء التجريبي

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).

المصدر