Triethylamine → 1-methyl-6-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

HRID 1729313Notes

Reaction equation

HRID 1729313 reaction equation
[C:1]1([O:7][CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[C:18]1[N:23]([CH3:24])[C:22](=[O:25])[NH:21][C:20](=[O:26])[CH:19]=1.C(N(CC)CC)C>C(O)(C)C>[CH3:24][N:23]1[C:18]([N:14]2[CH2:15][CH2:16][N:11]([CH2:10][CH2:9][CH2:8][O:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)[CH2:12][CH2:13]2)=[CH:19][C:20](=[O:26])[NH:21][C:22]1=[O:25]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27603511-(3-Phenoxypropyl)piperazineHCID 3015589Uracil, 6-chloro-1-methyl-

Product 1

HCID 190118701-methyl-6-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedioneYield 68.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1.3 g of 1-(3-phenyloxypropyl)piperazine and 0.5 g of 6-chloro-1-methyl-2,4(1H,3H)-pyrimidinedione were dissolved in 15 ml of isopropanol, and 2.7 ml of triethylamine was then added. Next, the solution was heated under reflux with stirring for 12 hours and then allowed to stand for cooling, and the solvent was distilled off. The resultant residue was dissolved in 100 ml of chloroform. The chloroform layer was washed with water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to obtain an oily product. This oily product was purified through a silica gel column chromatograph (chloroform/methanol=30/1 in volume ratio), thereby obtaining 0.73 g of 1-methyl-6-[4-(3-phenoxypropyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperatureNext, the solution was heated
  2. temperatureunder reflux
  3. temperaturefor cooling
  4. distillationthe solvent was distilled off
  5. dissolutionThe resultant residue was dissolved in 100 ml of chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customto obtain an oily product
  10. customThis oily product was purified through a silica gel column chromatograph (chloroform/methanol=30/1 in volume ratio)

Sources & evidence

ORD record
ord-7398bf8ce5ba4f0196340b40394907b1
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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