5-Iodouracil → HCID 10855712, compound

Participants

Reaction Conditions

Reaction Steps

5-iodouracil (340 mg, 1.43 mmol), the (fluorovinyl)stannane (600 mg, 1.8 mmol, prepared above in step C), tetrakis(triphenylphosphine)palladium(O) (approximately 20 mg) and dimethylformamide (4 mL) are combined and heated at 100° C. for 2 hours under an atmosphere of nitrogen. The reaction is then cooled to room temperature and the solvent removed under high vacuum. The residue is purified by flash chromatography (8% methanol/methylene chloride). The fraction containing the product is azeotroped with methylene chloride and then slurried in methylene chloride/ether. The solid is collected by filtration and then recrystallized from water (3 mL) to provide after filtration a light tan solid (60.5 mg). The filtrate is concentrated under vacuum and the residue is purified by radial chromatography (6% methanol/methylene chloride) to provide an additional 10 mg to provide a total of 70.5 mg (45%) of title compound. This is combined with 70 mg from another similar run and then purified again by radial chromatography (6% methanol/methylene chloride) to provide 91 mg of title compound as a buff colored solid after drying under high vacuum; mp 235°-238° C.

Provenance & Evidence