Tetrahydrofuran → 1,3-dimethyl-6-{4-[2-(4-nitrobenzoyloxy)ethyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

HRID 1085255Notes

Reaction equation

HRID 1085255 reaction equation
O1CCCC1.[N+:6]([C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1)([O-:8])=[O:7].[CH3:18][N:19]1[C:24]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][OH:33])[CH2:27][CH2:26]2)=[CH:23][C:22](=[O:34])[N:21]([CH3:35])[C:20]1=[O:36]>C(N(CC)CC)C>[CH3:18][N:19]1[C:24]([N:25]2[CH2:30][CH2:29][N:28]([CH2:31][CH2:32][O:33][C:13](=[O:14])[C:12]3[CH:11]=[CH:10][C:9]([N+:6]([O-:8])=[O:7])=[CH:17][CH:16]=3)[CH2:27][CH2:26]2)=[CH:23][C:22](=[O:34])[N:21]([CH3:35])[C:20]1=[O:36]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 85024-Nitrobenzoyl chlorideHCID 99702521,3-dimethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione2×

Product 1

HCID 200613501,3-dimethyl-6-{4-[2-(4-nitrobenzoyloxy)ethyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 5 ml of tetrahydrofuran were added 0.5 g of 4-nitrobenzoyl chloride, 0.47 g of 1,3-dimethyl-6-[4-(2-hydroxyethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (compound 41) and 1.5 ml of triethylamine, and the resulting mixture was stirred at room temperature overnight. Afterward, the used solvent was distilled off under reduced pressure, and the residue was then dissolved in chloroform. The resulting chloroform solution was washed with water, then dried over anhydrous sodium sulfate, and concentrated to dryness, thereby obtaining a crude product. The latter was then purified through a silica gel column chromatograph (chloroform/methanol=40/1 in terms of volume ratio) in order to obtain 1,3-dimethyl-6-{4-[2-(4-nitrobenzoyloxy)ethyl]piperazin-1-yl}-2,4(1H,3H)-pyrimidinedione. Next, this pyrimidinedione derivative was treated with an oxalic acid/methanol solution in a usual manner to prepare 0.84 g of 1,3-dimethyl-6-{4-[2-(4-nitrobenzoyloxy)ethyl]piperazine-1-yl}-2,4(1H,3H)-pyrimidinedione oxalate (compound 40).

Workup

  1. distillationAfterward, the used solvent was distilled off under reduced pressure
  2. dissolutionthe residue was then dissolved in chloroform
  3. washThe resulting chloroform solution was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated to dryness
  6. customobtaining a crude product
  7. customThe latter was then purified through a silica gel column chromatograph (chloroform/methanol=40/1 in terms of volume ratio) in order

Sources & evidence

ORD record
ord-a9bbc805cc3d42469aecd5b19f582d13
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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