Uridine → HCID 69539402, compound

Participants

Reaction Steps

To 10.0 g of 3′,5′-O-bis(4-chlorobenzoyl)-2′-deoxyuridine was added 50 mL of acetonitrile, 4.0 g of triethylamine, and 2.4 g (1.2 times moles based on the uridine derivative) of 1-methylpiperidine, and the resulting mixture was stirred in an ice bath. To this, the solution of 7.5 g of p-toluenesulfonyl chloride in 25 ml of acetonitrile was added dropwise over 1 hour at −1.5° C. or below −1.5° C. After the completion of addition, the mixture was stirred for 1 hour. Then, 50 mL of 28% ammonia water was added dropwise over 20 minutes at 4.5° C. or below 4.5° C. After the completion of addition, the mixture was stirred for 2.5 hours. The precipitated crystals were filtered and washed with acetonitrile to give 7.93 g of 3′,5′-O-bis(4-chlorobenzoyl) -2′-deoxycytidine. Yield 79.5%.

Provenance & Evidence