5-Fluorouracil → n1-(2-Maleinimidoethyloxycarbonyl)-5-fluorouracil

Participants

Reaction Steps

500 mg (3.84 mmol) 5-fluorouracil were dissolved in 100 ml of tetrahydrofuran and diluted with 505 mg (696 μl; 4.99 mmol) of triethylamine. To this solution, 1016 mg (4.99 mmol) of 2-maleinimidoethyl chloroformate, dissolved in 100 ml of tetrahydrofuran, were added drop-wise and the set-up was stirred for 15 h at room temperature. Then, the solvent was removed under the water jet vacuum and the residue purified using column chromatography (LOBAR®-column; running medium: acetic acid/hexane 1.5/1; yield: 61%); melting point: 132° C., Rf-value: 0.64 (diol; acetic acid/hexane 2/1); calculated: C: 44.29% H: 2.68% N: 14.09%, (C11H8N3O6F); found: C: 44.29% H: 2.68% N: 13.58%.

Provenance & Evidence