Pyridine → HCID 67281958, compound

Participants

Reaction Steps

To the 2′-O-(2-cyanoethoxymethyl)-5-methyluridine (20.7 g, 60.6 mmol) obtained in Step 2 was added anhydrous tetrahydrofuran (150 mL), anhydrous pyridine (150 mL), activated Molecular Sieves 4A (50 g), and 4,4′-dimethoxytrityl chloride (22.6 g, 66.7 mmol), and the mixture was stirred overnight at room temperature. After completion of the reaction, methanol (5 mL) was added to the reaction solution and the mixture was stirred for 15 min. The reaction solution was then filtered under aspiration and washed with ethyl acetate, and the filtrate was concentrated. To the residue was added aqueous saturated sodium bicarbonate solution and the mixture was extracted with ethyl acetate. The organic layer was washed with aqueous saturated brine, dried over magnesium sulfate, filtered and concentrated. The residue was subjected to silica gel chromatography to give 5′-O-(4,4′-dimethoxytrityl)-2′-O-(2-cyanoethoxymethyl)-5-methyluridine (35.6 g; yield 91.2%).

Provenance & Evidence