Idoxuridine → 5-[3-(2-Trifluoroacetamidoethoxy)propynyl]-2'-deoxyuridine

A mixture of 5-iodo-2'-deoxyuridine (3.54 g, 10 mmol), copper(1) iodide (0.19 g, 1 mmol) and tetrakis(triphenylphosphine)palladium(O) (0.58 g, 0.5 mmol) is dried in vacuo at 60° for 3 hours and placed under argon. A suspension of the mixture in dry DMF (20 ml) is stirred under argon and treated with dry triethylamine (1.7 ml, 12 mmol) followed by 3-(2-Trifluoroacetamidoethoxy)propyne (3.17 g, 16 mmol). The mixture is cooled at room temperature in a water bath and stirred for 17 hours. The mixture is treated with 2% acetic acid (100 ml), the catalyst is removed by filtration and washed with 50% methanol. The filtrates are combined and passed onto a LiChroprep RP-18 column (5×25 cm), the column is washed, then eluted with 1% acetic acid in 50% (v/v) methanol. The fractions with the main product are combined, evaporated, and dried in vacuo. The resultant foam is stirred with 150 ml of ether to give crystalline product; yield 3.6 g (85%); m.p. 145°-152°.

1. customis dried in vacuo at 60° for 3 hours
2. additionA suspension of the mixture in dry DMF (20 ml)
3. stirringstirred for 17 hours
4. customthe catalyst is removed by filtration
5. washwashed with 50% methanol
6. washthe column is washed
7. washeluted with 1% acetic acid in 50% (v/v) methanol
8. customevaporated
9. customdried in vacuo
10. stirringThe resultant foam is stirred with 150 ml of ether
11. customto give crystalline product

ORD-Eintrag

ord-02428669ff2f4425bf53c04ba4f9732e

Quelldatensatz

uspto-grants-1998_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05849482