Sodium hydride → 4-chloro-1-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)imidazo[4,5-c]-pyridine

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Reaction Steps

A solution of 2.4 g of sodium hydride, 15.4 g of 4-chloro-1H-imidazo[4,5-c]pyridine, and 200 ml of dry dimethylformamide (DMF) is stirred at 50° C. for 5 minutes, cooled, and added to 43.9 g of 2,3,5-tri-O-benzyl-α-D-arabinofuranosyl chloride. The solution is kept at ambient temperature for two hours, concentrated in vacuo, and distributed between a mixture of ethyl acetate-water. Chromatography of the dried ethyl acetate layer over silica gel with 4:1 benzene-ethyl acetate provides 49.6 g of syrupy 4-chloro-1-(2,3,5-tri-O-benzyl-β-D-arabinofuranosyl)imidazo[4,5-c]-pyridine.

Provenance & Evidence