5-Iodouracil → HCID 10855712, compound

HRID 1721745Notes

Reaction equation

HRID 1721745 reaction equation
I[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.[F:10][CH:11]=[CH:12][SnH3]>C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Pd].CN(C)C=O>[F:10][C:11]([C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)=[CH2:12]

Participants

5

Reactant 2

HCID 696725-IodouracilHCID 131719395HCID 131719395, compound

Product 1

HCID 10855712HCID 10855712, compoundYield 45%

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

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.

Workup

  1. temperatureThe reaction is then cooled to room temperature
  2. customthe solvent removed under high vacuum
  3. customThe residue is purified by flash chromatography (8% methanol/methylene chloride)
  4. additionThe fraction containing the product
  5. customis azeotroped with methylene chloride
  6. filtrationThe solid is collected by filtration
  7. customrecrystallized from water (3 mL)
  8. customto provide
  9. filtrationafter filtration a light tan solid (60.5 mg)
  10. concentrationThe filtrate is concentrated under vacuum
  11. customthe residue is purified by radial chromatography (6% methanol/methylene chloride)
  12. customto provide an additional 10 mg

Sources & evidence

ORD record
ord-e9932dcf56994679b935a3d46ac1dc8e
Source dataset
uspto-grants-1996_04
Patent number
US05512678

Reaction notes

Loading…