N-Hydroxyphthalimide → 4-Chloro-7-[2-c-methyl-3,5-bis-o-(2,4-dichlorophenylmethyl)-beta-d-ribofuranosyl]-5-(2-phthalimidooxyethyl)-7h-pyrrolo[2,3-d]pyrimidine

Participants

Reaction Steps

To a solution of the compound 2.6 (359.0 mg, 0.54 mmol) in THF (10 mL) were added triphenylphosphine (215.0 mg, 0.82 mmol) and N-hydroxyphthalimide (132.0 mg, 0.0.81 mmol) followed by diethylazodicarboxylate (DEAD) (153 μL, 0.88 mmol), and the solution was stirred overnight at room temperature. The reaction mixture was diluted by adding 10 mL of CH2Cl2 and 10 mL of water. The aqueous layer was extracted three times with CH2Cl2, dried over Na2SO4, filtered and evaporated. The product was purified by flash column chromatography using 15-20% EtOAc in hexanes as eluent gave the desired compound 2.7 (369 mg, 85%) as a white solid.

Provenance & Evidence