Tetrabutylammonium Fluoride → N-[3-(4,4'-dimethoxytrityloxymethyl)benzyl]-N'-[(6-hydroxymethylpyridin-2-yl)methyl]urea

Participants

Reaction Steps

To a suspension of N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-{[6-(tert-butyldimethylsilyloxy)methylpyridin-2-yl]methyl}urea (6) (410 mg, 0.57 mmol) in THF (2.2 mL), which was stirred, was added dropwise a solution of 1.0M TBAF in THF (0.64 mL), and stirred for 4 hours at a room temperature under Ar atmosphere. TLC was used to confirm there was no starting material in the reaction mixture. Then, the reaction mixture was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (CHCl3:MeOH=20:1) to give N-[3-(4,4′-dimethoxytrityloxymethyl)benzyl]-N′-[(6-hydroxymethylpyridin-2-yl)methyl]urea (7) (336 mg, 98%) as colorless crystals.

Provenance & Evidence