Diisopropylamine → Doxifluridine

Participants

Reaction Steps

To a suspension of 20 g (0.053 m) of 5′-deoxy-5′-iodo-5-fluoro uridine in a mixture of 60 ml of ethanol and 40 ml of isopropanol, 15.2 ml (0.108 m) of diisopropylamine are added, then 3 g of 5% Pd/C are added thereinto and the mixture is hydrogenated at about 1-bar pressure for 14 hours. After removal of the catalyst by filtration, the solution is concentrated under vacuum until a solid residue is obtained, which is crystallized with a mixture ethanol/isopropanol=60/40 v/v; after 8 hours the product is filtered, washed with said mixture and dried at 45° C. for 15 hours. Thus, 11,6 g (yield—89% of the theoretical) of 5′-deoxy-5-fluorouridine M.p.=187÷188° C., puritya (HPLC)=99,75% and [α]D=+18.2° (c=0.42, H2O).

Provenance & Evidence