5-Aminoimidazole-4-carboxamide hydrochloride → 4-(3,4-Dimethoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamide

HRID 477453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 477453
C[N:2]([CH3:17])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[C:9]([O:15][CH3:16])[CH:8]=1)=O.Cl.NC1[N:21]=[CH:22][NH:23][C:24]=1[C:25]([NH2:27])=[O:26].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH3:16][O:15][C:9]1[CH:8]=[C:7]([C:5]2[N:21]3[CH:22]=[N:23][C:24]([C:25]([NH2:27])=[O:26])=[C:17]3[N:2]=[CH:3][CH:4]=2)[CH:12]=[CH:11][C:10]=1[O:13][CH3:14]

Komponenten

5

Edukt 3

HCID 661465-Aminoimidazole-4-carboxamide hydrochlorideHCID 516892Sodium BicarbonateHCID 1481361(E)-1-(3,4-dimethoxyphenyl)-3-(dimethylamino)-2-propen-1-one

Produkt 1

HCID 146774754-(3,4-Dimethoxyphenyl)imidazo[1,5-a]pyrimidine-8-carboxamideAusbeute 53,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A stirred mixture of 15.0 g of 3-dimethylamino-3',4'-dimethoxyacrylophenone (prepared as described in Example 6) and 8.0 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 to give an oil. The oil solidified on standing at room temperature, and this was treated with 200 ml of saturated sodium bicarbonate solution and then it was filtered to collect the crystals. The material was treated by boiling with 700 ml of ethanol and then was filtered. The solid was recrystallized from methanol-chloroform to give 7.9 g of the desired product, mp 262°-265° C.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customThe solvent was evaporated in vacuo
  4. customto give an oil
  5. customon standing at room temperature
  6. filtrationit was filtered
  7. customto collect the crystals
  8. additionThe material was treated
  9. filtrationwas filtered
  10. customThe solid was recrystallized from methanol-chloroform

Quellen und Nachweise

ORD-Eintrag
ord-b478f80c5cbd4adb9a7f78e0589823e6
Quelldatensatz
uspto-grants-1989_12
Patentnummer
US04888345

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