反应详情

温度

150 °C

A mixture of 5-methyluridine (16.77 g, 69.2 mmol), diphenyl carbonate (17.8 g, 83.1 mmol) and sodium bicarbonate (100 mg) in hexamethylphosphoramide (175 ml) was heated to 150° C. with stirring until evolution of CO2 ceased (approximately 1 hr). The reaction mixture was cooled and then poured into diethylether (1 l) while stirring to furnish a brown gum. Repeated washings with diethylether (4×250 ml) furnished a straw colored hygroscopic powder. The solid was purified by short column chromatography on silica gel (400 g). Pooling and concentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (85:15, v/v) furnished the title compound as a straw colored solid (12 g, 77.3%) which crystallized from EtOH as long needles, m.p. 226-227° C.

1. custom(approximately 1 hr)
2. temperatureThe reaction mixture was cooled
3. customto furnish a brown gum
4. washRepeated washings with diethylether (4×250 ml)
5. customfurnished a straw colored hygroscopic powder
6. customThe solid was purified by short column chromatography on silica gel (400 g)
7. washPooling and concentration of appropriate fractions, which were eluted with CH2Cl2-MeOH (85:15, v/v)