Oxygen → 5-((trimethylsilyl)ethynyl)pyrimidine-2,4(1H,3H)-dione
Reaction equation
I[C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1.O=O.[CH3:12][Si:13]([C:16]#[CH:17])([CH3:15])[CH3:14]>C(N(CC)CC)C.CN(C=O)C.[Pd](Cl)Cl.[Cu]I>[CH3:12][Si:13]([C:16]#[C:17][C:2]1[C:3](=[O:9])[NH:4][C:5](=[O:8])[NH:6][CH:7]=1)([CH3:15])[CH3:14]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 50 °C
Procedure
A solution of 5-iodouracil (8g, 30mmol) in redistilled triethylamine (500 mL) and dry DMF (10mL) was deqassed with oxygen-free nitrogen for 15 minutes. Bis(triphenylophosphine palladium (II) chloride (0.5g), copper (I) iodide (0.5g) and trimethylsilylacetylene (10g, 102mmol ) were than added and the mixture was heated with stirring at 50° C for 24 hours. The cooled reaction mixture was filtered, the filtrate evaporated to dryness and the residue dissolved in dichloromethane (500mL). The organic solution was washed with a 2% aqueous solution of disodium EDTA (3×250mL), water (3×200mL), dried (Na2SO4) and evaporated to dryness. The residue was triturated with ethanol to give the first crop of the title compound. The solid filtered from the reaction mixture was also found to contain the required product but in a more impure form and so was worked up as above in a separate batch to give a second crop.
Workup
- additionthan added
- temperaturethe mixture was heated
- customThe cooled reaction mixture
- filtrationwas filtered
- customthe filtrate evaporated to dryness
- dissolutionthe residue dissolved in dichloromethane (500mL)
- washThe organic solution was washed with a 2% aqueous solution of disodium EDTA (3×250mL), water (3×200mL)
- dry with materialdried (Na2SO4)
- customevaporated to dryness
- customThe residue was triturated with ethanol
Sources & evidence
- ORD record
- ord-3978ed5f70a4473dbdbc9c1ca1c3c875
- Source dataset
- uspto-grants-1998_10
- Patent number
- US05817664
Reaction notes
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