Ibacitabine → Deoxycytidine

Participants

Reaction Steps

Into acetonitrile (30 mL), 1.0 g of 5-iodo-2′-deoxycytidine [the compound (57) in the above synthesis route], (manufactured by Wako Pure Chemical Industries, Ltd.), was suspended, and after the addition of o-bis(trimethylsilyl)acetamide (TMS-Acetamide) (3 mL) by purging with Ar, the solution was subjected to stirring under refluxing for 2 hours. After cooling the reaction solution to room temperature, bis(acetonitrile)dichloropalladium (II) [PdCl2(CH3CN)2] (40 mg) and 2 g of the partial linker A [the compound (53) in the above synthesis route] were added to further stirring at 50 to 60° C. for 20 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The residue was subjected to purification by using silica gel column (elution liquid: trichloromethane/methanol=9/1) to give 720 mg of a 2′-deoxycytidine derivative [the compound (58) in the above synthesis route] by crystallization from diethyl ether (yield; 67.3%).

Provenance & Evidence