Pyridine → 7-(2-Thienyl)-3-(beta-D-ribofuranosyl)-3H-imidazo[4,5-b]pyridine

Participants

Reaction Steps

Compound 9 (290 mg, 0.47 mmol) was azeotroped with pyridine, followed by addition of THF (2.4 ml) and diisopropylethylamine (123 μl, 0.7 mmol). To this solution, 2-cyanoethyl-N,N-diisopropylamino chloro phosphoroamidite (115 μl, 0.52 mmol) was added and stirred at room temperature for 1 hour. After addition of methanol (50 μl), the reaction mixture was diluted with ethyl acetate:triethylaime (20:1, v/v) and partitioned with 5% aqueous NaHCO3. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous sodium sulfate, concentrated and then purified on a silica gel column to give Compound 11 (345 mg, 90%).

Provenance & Evidence