5-Aminoimidazole-4-carboxamide hydrochloride → 4-Phenylimidazo[1,5-a]pyrimidine-8-carboxamide

HRID 477451

Reaktionsgleichung

Reaktionsgleichung von HRID 477451
Cl.[NH2:2][C:3]1[N:4]=[CH:5][NH:6][C:7]=1[C:8]([NH2:10])=[O:9].CN(C)[CH:13]=[CH:14][C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=O.C(=O)(O)[O-].[Na+]>C(O)(=O)C.ClCCl>[C:17]1([C:15]2[N:4]3[CH:5]=[N:6][C:7]([C:8]([NH2:10])=[O:9])=[C:3]3[N:2]=[CH:13][CH:14]=2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 516892Sodium Bicarbonate

Produkt 1

HCID 146774704-Phenylimidazo[1,5-a]pyrimidine-8-carboxamideAusbeute 43,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A stirred mixture of 11.0 g of 4-amino-5-imidazolecarboxamide hydrochloride and 15.0 g of 3-dimethylaminoacrylophenone (prepared as described in Example 1) in 120 ml of glacial acetic acid was heated at reflux for 4 hours. The solvent was evaporated in vacuo to give a dark oil which was dissolved in dichloromethane, then treated by stirring with saturated sodium bicarbonate. The organic solvent was evaporated and the remaining mixture was filtered and the solid was washed with water, dried, and then was recrystallized from ethanol to give 7.08 g of the desired product as a yellow solid, mp 226°-228° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. customThe solvent was evaporated in vacuo
  4. customto give a dark oil which
  5. additiontreated
  6. customThe organic solvent was evaporated
  7. filtrationthe remaining mixture was filtered
  8. washthe solid was washed with water
  9. customdried
  10. customwas recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-816a2f8c0a064c0a9685c614ac62d7c6
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888345

Verknüpfte Notizen

Wird geladen…