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Hydrochloric Acid → 1H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-

HRID 1081814
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1081814
[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](O)=O.S(Cl)(Cl)=O.[NH2:21][C:22]1[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=1[NH2:28].Cl>N1C=CC=CC=1.[OH-].[Na+].O1CCOCC1.O.C(Cl)Cl>[Cl:1][C:2]1[C:12]([O:13][CH3:14])=[C:11]([O:15][CH3:16])[CH:10]=[CH:9][C:3]=1/[CH:4]=[CH:5]/[C:6]1[NH:21][C:22]2[C:23](=[O:32])[N:24]([CH3:31])[C:25](=[O:30])[N:26]([CH3:29])[C:27]=2[N:28]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

10

Edukt 4

HCID 313Hydrochloric AcidHCID 24386Thionyl ChlorideHCID 795015,6-Diamino-1,3-dimethyluracilHCID 27749672-Chloro-3,4-dimethoxycinnamic acid

Produkt 1

HCID 64488901H-Purine-2,6-dione, 3,7-dihydro-8-(2-(2-chloro-3,4-dimethoxyphenyl)ethenyl)-1,3-dimethyl-, (E)-Ausbeute 30 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

2-Chloro-3,4-dimethoxycinnamic acid (3.93 g, 16.2 mmol) was dissolved in 57 ml of pyridine. To the solution was added 1.26 ml (17.6 mmol) of thionyl chloride under ice cooling, and the mixture was stirred at 60° C. for 1.5 hours. Methylene chloride (58 ml) containing 2.50g (14.7 mmol) of 5,6-diamino-1,3-dimethyluracil was added dropwise to the solution under ice cooling, and the reaction solution was stirred at room temperature for further 40 minutes. The deposited crystals were collected by filtration and the obtained crude crystals were dissolved in a mixture of 68 ml of an aqueous 2N sodium hydroxide solution, 68 ml of dioxane, and 34 ml of water, followed by heating under reflux for 30 minutes. After cooling, the solution was neutralized with a concentrated aqueous solution of hydrochloric acid, and the deposited crystals were collected by filtration. The collected crystals were washed with water, dried, and recrystallized from dimethylformamide/water to give 1.55 g (yield 30%) of Compound 114 as pale yellow needles.

Aufarbeitung

  1. additionwas added dropwise to the solution under ice cooling
  2. stirringthe reaction solution was stirred at room temperature for further 40 minutes
  3. filtrationThe deposited crystals were collected by filtration
  4. customthe obtained crude crystals
  5. temperatureby heating
  6. temperatureunder reflux for 30 minutes
  7. temperatureAfter cooling
  8. filtrationthe deposited crystals were collected by filtration
  9. washThe collected crystals were washed with water
  10. customdried
  11. customrecrystallized from dimethylformamide/water

Quellen und Nachweise

ORD-Eintrag
ord-7b08c47654fc48ec961239313e2ce544
Quelldatensatz
uspto-grants-1996_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05587378

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