Sodium Hydroxide → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3-bromophenyl)ethenyl)-1,3-diethyl-, (E)-

HRID 1378994

Reaktionsgleichung

Reaktionsgleichung von HRID 1378994
[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](O)=O.Cl.C(N(CC)CCCN=C=NCC)C.[NH2:27][C:28]1[C:29](=[O:40])[N:30]([CH2:38][CH3:39])[C:31](=[O:37])[N:32]([CH2:35][CH3:36])[C:33]=1[NH2:34].[OH-].[Na+]>O.O1CCOCC1>[Br:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)/[CH:5]=[CH:6]/[C:7]1[NH:27][C:28]2[C:29](=[O:40])[N:30]([CH2:38][CH3:39])[C:31](=[O:37])[N:32]([CH2:35][CH3:36])[C:33]=2[N:34]=1

Komponenten

7

Edukt 4

HCID 14798Sodium HydroxideHCID 362513-(3-Bromophenyl)acrylic acidHCID 45721335,6-Diamino-1,3-diethyluracilHCID 99645121-(3-Diethylaminopropyl)-3-ethylcarbodiimide hydrochloride

Produkt 1

HCID 64489301H-Purine-2,6-dione, 3,7-dihydro-8-(2-(3-bromophenyl)ethenyl)-1,3-diethyl-, (E)-Ausbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

3-Bromocinnamic acid (2.52 g, 11.1 mmol) and 3-(3-diethylaminopropyl)-1-ethylcarbodiimide hydrochloride (2.90 g, 15.2 mmol) were added to a solution of 5,6-diamino-1,3-diethyluracil (2.0 g, 10.1 mmol) in a dioxane (34 ml)-water (68 ml) mixture, and the resulting mixture was stirred at room temperature for 40 minutes while keeping the pH at 5.5. A 4N aqueous solution of sodium hydroxide was added thereto to adjust the pH to >14, and the mixture was heated under reflux for 20 minutes. After cooling, the mixture was neutralized and the precipitated crystals were collected by filtration. The obtained crude crystals were recrystallized from tetrahydrofuran/water to give 2.01 g (yield 37%) of Compound g as pale green plates.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 20 minutes
  3. temperatureAfter cooling
  4. filtrationthe precipitated crystals were collected by filtration
  5. customThe obtained crude crystals
  6. customwere recrystallized from tetrahydrofuran/water

Quellen und Nachweise

ORD-Eintrag
ord-e21f30852c764a038034e8861ee1b35c
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05670498

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