N-Iodosuccinimide → 6-Chloro-7-iodo-7-deazapurine

Participants

Reaction Steps

6-Chloro-7-deazapurine 10.75 g (70 mmol) and N-iodosuccinimide (16.8 g, 75 mmol) were dissolved in 400 ml of dry DMF and left at ambient temperature in the darkness over night. The solvent was evaporated. The dark residue was distributed between 500 ml of ethyl acetate and 150 ml of 10% Na2SO3. Organic fraction was washed with 10% Na2SO3 (2×100 ml), brine (150 ml), dried over Na2SO4 and evaporated. The yellow residue was crystallized from ethanol to yield 16.2 g (83%) of the title compound as off white crystals. The mother liquid was evaporated, dissolved in toluene, and purified by flush chromatography on silica gel (7×4 cm). The column was washed with toluene until the eluent was colorless than the title compound was eluted with 5% ethyl acetate in toluene to give additional 3.5 g of the title product.

Provenance & Evidence