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

HRID 477450

Reaktionsgleichung

Reaktionsgleichung von HRID 477450
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

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-b4225ec8f3b146fb9fffca1c71b90481
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888345

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