1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 8-((6,7-dimethoxy-1-methylisoquinolin-4-yl)methyl)-3-isobutyl-1-methyl-1H-purine-2,6(3H,7H)-dione

HRID 900715Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 900715
Cl.CN(C)CCCN=C=NCC.[NH2:13][C:14]1[C:15](=[O:27])[N:16]([CH3:26])[C:17](=[O:25])[N:18]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:19]=1[NH2:20].[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[C:36]([CH3:42])=[N:35][CH:34]=[C:33]2[CH2:43][C:44](O)=O>CO.O>[CH3:28][O:29][C:30]1[CH:31]=[C:32]2[C:37](=[CH:38][C:39]=1[O:40][CH3:41])[C:36]([CH3:42])=[N:35][CH:34]=[C:33]2[CH2:43][C:44]1[NH:13][C:14]2[C:15](=[O:27])[N:16]([CH3:26])[C:17](=[O:25])[N:18]([CH2:21][CH:22]([CH3:23])[CH3:24])[C:19]=2[N:20]=1

Komponenten

6

Edukt 3

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 41103394,5-Diamino-3-isobutyl-1-methylpyrimidine-2,6-dioneHCID 22226535(6,7-Dimethoxy-1-methyl-isoquinolin-4-yl)-acetic acid

Produkt 1

HCID 102250638-((6,7-dimethoxy-1-methylisoquinolin-4-yl)methyl)-3-isobutyl-1-methyl-1H-purine-2,6(3H,7H)-dione

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

1-(3-Dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.201 g, 1.30 mmol) is added to 5,6-diamino-1-isobutyl-3-methyl-1H-pyrimidine-2,4-dione (0.223 g, 1.05 mmol)) and (6,7-dimethoxy-1-methyl-isoquinolin-4-yl)-acetic acid (0.25 g, 0.96 mmol) in methanol (5 ml) and water (1 ml) and the mixture is stirred at ambient temperature for 16 hours. The methanol is evaporated and the resultant solid collected by filtration, taken into methanol (5 ml) and 5M aqueous sodium hydroxide (0.5 ml) is added. The reaction is heated to reflux for 1 hour, cooled to ambient temperature and evaporated. The residue is dissolved in water and extracted with dichloromethane, the combined organic extracts are dried over sodium sulfate and evaporated to afford 8-(6,7-dimethoxy-1-methyl-isoquinolin-4-ylmethyl)-3-isobutyl-1-methyl-3,7-dihydro-purine-2,6-dione, M+ 437.

Aufarbeitung

  1. customThe methanol is evaporated
  2. filtrationthe resultant solid collected by filtration
  3. additionis added
  4. temperatureThe reaction is heated
  5. temperatureto reflux for 1 hour
  6. temperaturecooled to ambient temperature
  7. customevaporated
  8. dissolutionThe residue is dissolved in water
  9. extractionextracted with dichloromethane
  10. dry with materialthe combined organic extracts are dried over sodium sulfate
  11. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-593f46409839475794b5cc86a3889f54
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07361661B2

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