Ethanol → 4-(m-Methoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 477452

Reaktionsgleichung

Reaktionsgleichung von HRID 477452
C[N:2]([CH3:15])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[CH:8]=1)=O.Cl.NC1[N:19]=[CH:20][NH:21][C:22]=1[C:23]([NH2:25])=[O:24].C(#N)C.C(O)C>C(O)(=O)C>[CH3:14][O:13][C:9]1[CH:8]=[C:7]([C:5]2[N:19]3[CH:20]=[N:21][C:22]([C:23]([NH2:25])=[O:24])=[C:15]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][CH:10]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 6342AcetonitrileHCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 425737963-Dimethylamino-3'-methoxyacrylophenone

Produkt 1

HCID 146774744-(m-Methoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamideAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A stirred mixture of 15.0 g of 3-dimethylamino-3'-methoxyacrylophenone (prepared as described in Example 5 and 9.2 g of 4-amino-5-imidazolecarboxamide hydrochloride in 150 ml of glacial acetic acid was heated at reflux for 24 hours. The solvent was evaporated in vacuo and the crystalline residue was treated with 100 ml of saturated sodium bicarbonate solution, filtered and washed with 200 ml of water to give yellow crystals. This material was treated with 400 ml of acetonitrile then with 600 ml of hot ethanol to give 9.9 g of the product of the example as yellow crystals, mp 249°-252° C.

Aufarbeitung

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 24 hours
  4. customThe solvent was evaporated in vacuo
  5. additionthe crystalline residue was treated with 100 ml of saturated sodium bicarbonate solution
  6. filtrationfiltered
  7. washwashed with 200 ml of water
  8. customto give yellow crystals

Quellen und Nachweise

ORD-Eintrag
ord-73767f1bc2024c24a26597c6068287f1
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888345

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