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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 477450Erstellt: 24. Oktober 2026

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

https://huagongshe.com/de/reaction/477450

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
Edukt5-Aminoimidazole-4-carboxamide hydrochlorideHCID 66146—
EduktSodium BicarbonateHCID 516892—
Edukt2',5'-Dichloro-3-dimethylaminoacrylophenoneHCID 2806206—
EduktMethylenechloride HexaneHCID 21226440—
LösungsmittelAcetic AcidHCID 176—
LösungsmittelDichloromethaneHCID 6344—
Produkt4-(2,5-Dichlorophenyl)imidazo[1,5-a]pyrimidine-8-carboxamideHCID 1467747374,3%

Reaktionsschritte

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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS04888345
Quelldatensatzuspto-grants-1989_12
ORD IDord-b4225ec8f3b146fb9fffca1c71b90481
Quellennotizuspto-grants-1989_12