Ibacitabine → Deoxycytidine

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%).

1. customby purging with Ar
2. temperatureunder refluxing for 2 hours
3. additionbis(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
4. stirringto further stirring at 50 to 60° C. for 20 hours
5. customAfter completion of the reaction
6. concentrationthe reaction solution was concentrated under reduced pressure
7. customThe residue was subjected to purification
8. washsilica gel column (elution liquid: trichloromethane/methanol=9/1)

ORD record

ord-56e368e2ff1949829d8678c72f13244f

Source dataset

uspto-grants-2014_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08921124B2