Triethylamine → HCID 20061283, compound

HRID 1085257Notes

Reaction equation

HRID 1085257 reaction equation
O1CCOC[CH2:2]1.[N+:7]([C:10]1[CH:19]=[CH:18][C:13]([C:14](=O)[CH2:15]Br)=[CH:12][CH:11]=1)([O-:9])=[O:8].[CH3:20][N:21]1[C:26]([N:27]2CCNCC2)=[CH:25][C:24](=[O:33])[N:23]([CH3:34])[C:22]1=[O:35].[CH2:36]([N:38]([CH2:41][CH3:42])[CH2:39][CH3:40])C>>[CH3:20][N:21]1[C:26]([NH:27][CH2:40][CH2:39][N:38]([CH2:36][CH2:15][CH2:14][C:13]2[CH:18]=[CH:19][C:10]([N+:7]([O-:9])=[O:8])=[CH:11][CH:12]=2)[CH:41]([CH3:42])[CH3:2])=[CH:25][C:24](=[O:33])[N:23]([CH3:34])[C:22]1=[O:35]

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 668402-Bromo-4'-nitroacetophenoneHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 20061283HCID 20061283, compound

Procedure

Next, to 150 ml of dioxane were added 4.88 g of the above prepared p-nitrophenacyl bromide, 4.48 g of 1,3-dimethyl-6-(1-piperazinyl)-2,4(1H,3H)-pyrimidinedione (compound 37) and 4.2 ml of triethylamine, and the solution was heated under reflux for 1 hour. Afterward, the reaction mixture was cooled to deposit crystals, and the latter were collected by filtration, dissolved in chloroform, washed with water, and dried (over anhydrous sodium sulfate). Afterward, the used solvent was distilled off, and methanol was then added to the residue so as to crystallize it. The resulting crystals were then collected by filtration, washed, and dried to obtain 4.02 g of 1,3-dimethyl-6-[4-(4-nitrophenacyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione (compound 43).

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfterward, the reaction mixture was cooled
  4. filtrationthe latter were collected by filtration
  5. dissolutiondissolved in chloroform
  6. washwashed with water
  7. dry with materialdried (over anhydrous sodium sulfate)
  8. distillationAfterward, the used solvent was distilled off
  9. additionmethanol was then added to the residue so as
  10. customto crystallize it
  11. filtrationThe resulting crystals were then collected by filtration
  12. washwashed
  13. customdried

Sources & evidence

ORD record
ord-3bb5e0cf74ca4a8ebb23c18cfb858034
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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