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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 1199942Erstellt: 26. Oktober 2026

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

https://huagongshe.com/reaction/1199942

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt5-Aminoimidazole-4-carboxamide hydrochlorideHCID 66146—
EduktSodium BicarbonateHCID 516892—
Edukt1-(3-Chlorophenyl)-3-(dimethylamino)-2-propen-1-oneHCID 730065—
LösungsmittelAcetic AcidHCID 176—
Produkt4-(3-Chlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamideHCID 1467747243,7%

Reaktionsschritte

A mixture of 13.9 g of 4-amino-5-imidazolecarboxamide hydrochloride, 24.0 g of 3'-chloro-3-dimethylaminoacrylophenone (U.S. Pat. No. 4,209,621, Ex. 50) and 200 ml of glacial acetic acid was heated at reflux for 5 hours. The liquid was evaporated in vacuo to give a yellow solid. The excess acid was neutralized with saturated sodium bicarbonate solution and this mixture was filtered and the solid was washed with water and then was dried. Recrystallization from ethanol-methanol gave 10.2 g of the desired product as yellow crystals, mp 252°-254° C.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04904658
Quelldatensatzuspto-grants-1990_02
ORD IDord-88695e327f1548d1979f4beef7f931dc
Quellennotizuspto-grants-1990_02