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

HRID 1085249Notes

Reaction equation

HRID 1085249 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:12][N:13]1[C:18]([NH:19][CH2:20][CH2:21]CNC2C=CC([N+]([O-])=O)=CC=2)=[CH:17][C:16](=[O:33])[N:15]([CH3:34])[C:14]1=[O:35].[CH2:36]([N:38](CC)CC)[CH3:37]>C(O)(C)C>[CH3:12][N:13]1[C:18]([N:19]2[CH2:20][CH2:21][N:38]([CH2:8][C:7]3[CH:10]=[CH:11][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:36][CH2:37]2)=[CH:17][C:16](=[O:33])[N:15]([CH3:34])[C:14]1=[O:35]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 660114-Nitrobenzyl bromideHCID 200612441,3-dimethyl-6-[3-(4-nitroanilino)propylamino]-2,4-(1H,3H)-pyrimidinedione2×

Product 1

HCID 104736221,3-dimethyl-6-[4-(4-nitrobenzyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

First, 0.48 g of 4-nitrobenzyl bromide, 0.5 g of 1,3-dimethyl-6-(piperazin -1-yl)-2,4(1H,3H)-pyrimidinedione (compound 2) and 0.5 ml of triethylamine were suspended in 5 ml of isopropanol, and the resulting suspension was then heated under reflux for 8 hours. Afterward, the used solvent was removed from the resulting reaction mixture by distillation under reduced pressure, and the residue was dissolved in chloroform and was then washed with water. The washed organic layer was dried over anhydrous sodium sulfate. Furthermore, the dried organic layer was subjected to distillation under reduced pressure so as to remove the solvent therefrom, and the residue was then purified through a silica gel column chromatograph (chloroform/methanol=50/1 to 20/1 in terms of volume ratio) in order to obtain 0.88 g of 1,3-dimethyl-6-[4-(4-nitrobenzyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperaturethe resulting suspension was then heated
  2. temperatureunder reflux for 8 hours
  3. customAfterward, the used solvent was removed from the resulting reaction mixture by distillation under reduced pressure
  4. dissolutionthe residue was dissolved in chloroform
  5. washwas then washed with water
  6. dry with materialThe washed organic layer was dried over anhydrous sodium sulfate
  7. distillationFurthermore, the dried organic layer was subjected to distillation under reduced pressure so as
  8. customto remove the solvent
  9. customthe residue was then purified through a silica gel column chromatograph (chloroform/methanol=50/1 to 20/1 in terms of volume ratio) in order

Sources & evidence

ORD record
ord-744d1405421e4baca24789681da47d84
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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