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5-Aminoimidazole-4-carboxamide hydrochloride → 4-(2,5-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 1199943
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1199943
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:19](=O)[CH:20]=[CH:21]N(C)C.C(=O)(O)[O-].[Na+].ClCCl.CCCCCC>C(O)(=O)C.ClCCl>[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=1[C:19]1[N:4]2[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]2[N:2]=[CH:21][CH:20]=1
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Komponenten

7

Edukt 4

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 28062062',5'-Dichloro-3-dimethylaminoacrylophenoneHCID 21226440Methylenechloride Hexane

Produkt 1

HCID 146774734-(2,5-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamideAusbeute 74,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 5.2 g of 4-amino-5-imidazolecarboxamide hydrochloride and 10.0 g of 2',5'-dichloro-3-dimethylaminoacrylophenone (prepared as described in Example 4) in 80 ml of glacial acetic acid was heated at reflux for 4 hours. Evaporation in vacuo gave a dark oil which was dissolved in dichloromethane and treated with saturated sodium bicarbonate. The organic layer was separated, washed with water then dried over anhydrous sodium sulfate. The dichloromethane solution was passed through a short column of hydrous magnesium silicate. Evaporation of the eluate gave a semi-solid which was treated with hot dichloromethane-hexane to give a yellow precipitate which was collected by filtration and dried to give 7.3 g of the product of the example, mp 230°-234° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customEvaporation in vacuo
  4. customgave a dark oil which
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialthen dried over anhydrous sodium sulfate
  8. customEvaporation of the eluate
  9. customgave a semi-solid which
  10. customto give a yellow precipitate which
  11. filtrationwas collected by filtration
  12. customdried

Quellen und Nachweise

ORD-Eintrag
ord-f5b3f9f1af7b4d62b7b9c7a11cbb4212
Quelldatensatz
uspto-grants-1990_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04904658

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