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3-(3,4,5-Trimethoxyphenyl)acrylic acid → 3-Propyl-8-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-3,7-dihydro-purine-2,6-dione

HRID 1292425
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1292425
[NH2:1][C:2]1[C:3](=[O:13])[NH:4][C:5](=[O:12])[N:6]([CH2:9][CH2:10][CH3:11])[C:7]=1[NH2:8].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH3:39][O:40][C:41]1[CH:42]=[C:43]([CH:49]=[C:50]([O:54][CH3:55])[C:51]=1[O:52][CH3:53])[CH:44]=[CH:45][C:46](O)=O>CN(C)C=O>[CH2:9]([N:6]1[C:7]2[N:8]=[C:46](/[CH:45]=[CH:44]/[C:43]3[CH:49]=[C:50]([O:54][CH3:55])[C:51]([O:52][CH3:53])=[C:41]([O:40][CH3:39])[CH:42]=3)[NH:1][C:2]=2[C:3](=[O:13])[NH:4][C:5]1=[O:12])[CH2:10][CH3:11]
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Komponenten

6

Edukt 4

HCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 106313415,6-Diamino-1-propyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Produkt 1

HCID 151708643-Propyl-8-[2-(3,4,5-trimethoxy-phenyl)-vinyl]-3,7-dihydro-purine-2,6-dioneAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5,6-Diamino-1-propyluracil (2.00 g, 11 mmol) was suspended in 40 ml of N,N-dimethylformamide. To the suspension were added 3.37 g (16 mmol) of N,N'-dicyclohexylcarbodiimide and 2.00 g (13 mmol) of 1-hydroxybenzotriazole. Then, 2.59 g (11 mmol) of 3,4,5-trimethoxycinnamic acid was slowly added thereto in several portions, and the mixture was stirred overnight at room temperature. After insoluble substances were removed by filtration, the filtrate was concentrated under reduced pressure and 40 ml of a 2N aqueous solution of sodium hydroxide was added to the residue. The mixture was heated under reflux for 30 minutes, followed by neutralization. Deposited crystals were collected by filtration and recrystallized from isopropanol/water to give 2.51 g (overall yield: 60%) of Compound 22 as a yellow powder.

Aufarbeitung

  1. customAfter insoluble substances were removed by filtration
  2. concentrationthe filtrate was concentrated under reduced pressure and 40 ml of a 2N aqueous solution of sodium hydroxide
  3. additionwas added to the residue
  4. temperatureThe mixture was heated
  5. temperatureunder reflux for 30 minutes
  6. filtrationDeposited crystals were collected by filtration
  7. customrecrystallized from isopropanol/water

Quellen und Nachweise

ORD-Eintrag
ord-038f24034db9491a8186406b565c0add
Quelldatensatz
uspto-grants-1998_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05756735

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