Triethylamine → HCID 9976610, compound

HRID 1729280Notes

Reaction equation

HRID 1729280 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([CH2:8][CH2:9]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[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].C(N(CC)CC)C>C(O)(C)C.C(Cl)(Cl)Cl>[CH3:13][N:14]1[C:19]([N:20]2[CH2:25][CH2:24][N:23]([CH2:9][CH2:8][C:7]3[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=3)[CH2:22][CH2:21]2)=[CH:18][C:17](=[O:26])[N:16]([CH3:27])[C:15]1=[O:28]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 792664-Nitrophenethyl bromideHCID 128168731,3-Dimethyl-6-(piperazin-1-yl)pyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 9976610HCID 9976610, compoundYield 70.1%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 6212ChloroformSolvent

Procedure

0.51 g of 4-nitrophenethyl bromide, 0.5 g of 1,3-dimethyl-6-[1-piperazinyl]-2,4(1H,3H)-pyrimidinedione (Compound b) and 0.5 ml of triethylamine were suspended in 5 ml of isopropanol, and the resultant suspension was heated under reflux for 8 hours. The solvent was distilled off from the resultant reaction mixture under reduced pressure, and the residue was then dissolved in chloroform. After washing with water, the washed organic layer was dried over anhydrous sodium sulfate. In addition, the dried organic layer was treated under reduced pressure, and the solvent was then distilled off. Afterward, the residue was purified through a silica gel column chromatograph (chloroform/methanol=50/1 to 20/1 in volume ratio) to obtain 0.58 g of 1,3-dimethyl-6-[4-(2-[4-nitrophenyl]ethyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. temperatureunder reflux for 8 hours
  2. distillationThe solvent was distilled off from the resultant
  3. customreaction mixture under reduced pressure
  4. washAfter washing with water
  5. dry with materialthe washed organic layer was dried over anhydrous sodium sulfate
  6. additionIn addition, the dried organic layer was treated under reduced pressure
  7. distillationthe solvent was then distilled off
  8. customAfterward, the residue was purified through a silica gel column chromatograph (chloroform/methanol=50/1 to 20/1 in volume ratio)

Sources & evidence

ORD record
ord-33bd67dcb11f40878c3f9b15e3ad0221
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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