Ethanol → 1,3-dimethyl-6-[4-(2-ethoxycarbonyl-2-phenylethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1032967Notes

Reaction equation

HRID 1032967 reaction equation
[C:1]1([CH:7]([CH2:11]Br)[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]2)=[CH:18][C:17](=[O:26])[N:16]([CH3:27])[C:15]1=[O:28].[CH2:29](N(CC)CC)[CH3:30].C(O)C>O1CCOCC1>[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][N:23]([CH2:11][CH:7]([C:8]([O:10][CH2:29][CH3:30])=[O:9])[C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH2:22][CH2:21]2)=[CH:18][C:17](=[O:26])[N:16]([CH3:27])[C:15]1=[O:28]

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 2282363-Bromo-2-phenylpropanoic acidHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 190270851,3-dimethyl-6-[4-(2-ethoxycarbonyl-2-phenylethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

8.1 g of α-phenyl-β-bromopropionic acid and 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione were dissolved in 90 ml of dioxane, and the solution was stirred at 90° C. for 30 minutes. 12 ml of triethylamine was added to this solution, followed by stirring at 90° C. for 1 hour. Afterward, 60 ml of ethanol was added, and the solution was then heated under reflux for 3 hours. The solvent was distilled off from the reaction solution under reduced pressure, and the resulting residue was then dissolved in chloroform. The obtained solution was washed with water and then dried over anhydrous sodium sulfate. Afterward, the solvent was distilled off under reduced pressure, and the resulting residue was then purified through a silica gel column chromatograph (chloroform), thereby obtaining 4.5 g of 1,3-dimethyl-6-[4-(2-ethoxycarbonyl-2-phenylethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. stirringby stirring at 90° C. for 1 hour
  2. temperaturethe solution was then heated
  3. temperatureunder reflux for 3 hours
  4. distillationThe solvent was distilled off from the reaction solution under reduced pressure
  5. dissolutionthe resulting residue was then dissolved in chloroform
  6. washThe obtained solution was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfterward, the solvent was distilled off under reduced pressure
  9. customthe resulting residue was then purified through a silica gel column chromatograph (chloroform)

Sources & evidence

ORD record
ord-b6179569103d4f128f1949b3660d7bb2
Source dataset
uspto-grants-1994_05
Patent number
US05308848

Reaction notes

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