5-prop-2-enyl-1H-pyrimidine-2,4-dione → HCID 14914594, compound

HRID 440716Notes

Reaction equation

HRID 440716 reaction equation
[CH2:1]([C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)[CH:2]=[CH2:3]>CCO>[CH:1](/[C:4]1[C:5](=[O:11])[NH:6][C:7](=[O:10])[NH:8][CH:9]=1)=[CH:2]\[CH3:3]

Participants

3

Reactant 1

HCID 2555375-prop-2-enyl-1H-pyrimidine-2,4-dione

Product 1

HCID 14914594HCID 14914594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5-allyluracil (80 mg; 0.5 mmol) in 95% aq. EtOH (50 ml) was added (Ph3P)3RhCl (90 mg; 0.1 mmol) and the mixture heated under reflux for 3 days. The solvent was evaporated and the product isolated by flash chromatography on SiO2 eluted with 5% MeOH-CH2Cl2. Yield 56 mg 70%; 200 MHz 1H-NMR DMSO-d6, δ: 11.0 (br s, 1H, NH); 7.42 (s, 1H, 6-H); 6.35-6.55 (qq, 1H =CH-Me); 5.95-6.1 (dd, 1H, --CH=); 1.74 (dd, 3H, CH3).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 days
  3. customThe solvent was evaporated
  4. customthe product isolated by flash chromatography on SiO2
  5. washeluted with 5% MeOH-CH2Cl2

Sources & evidence

ORD record
ord-3d6f6e3d90c54bb29475ada005308464
Source dataset
uspto-grants-1996_05
Patent number
US05521163

Reaction notes

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