Pyridine → HCID 67259612, compound

Participants

Reaction Steps

Anhydrous pyridine (3.64 mL) was added to a solution of 5′-O-(4,4′-dimethoxitrityl)-1-N-methylpseudouridine (2.67 g, 4.48 mmol) and AgNO3 (934 mg, 5.69 mmol) in dry THF (32 mL) and stirred at room temperature for 20 min under an argon atmosphere. Followed by addition of tert-butyldimethylsilyl chloride (934 mg, 5.87 mmol) in dry THF (3 mL) and stirred at the same temperature for 3-4 h. The solids were filtered off and the filtrate was concentrated to a crude residue which was applied to a column of silica gel which was saturated with 2% triethylamine in hexanes, and eluted with hexane-ethyl acetate (1:1) to give a pure title compound (780 mg, 25%), and 5′-O-(4,4′-dimethoxitrityl)-3′-O-(tert-butyldimethylsilyl)-1-methylpseudouridine (800 mg, 25%) as amorphous solid.

Provenance & Evidence