Water → HCID 131710073, compound

Participants

Reaction Steps

N-Ethyl-N-(3,4-dihydro-5-methyl-7-propylimidazo [5,1-f]-as-triazin-2-yl)acetamide, hydrochloride (Example 7) (4.1 g.) and lithium aluminium hydride (3.3 g.) in a mixture of dimethyl digol (130 ml.) and diethyl digol (150 ml.) were heated under reflux for 24 hours and cooled. Water (3.37 ml.) was added followed by aqueous sodium hydroxide (3.3 ml.) and water (9.8 ml.). The solid was filtered off and the filtrate was evaporated. The residue was chromatographed on active alumina (300 g.) using ethyl acetate as eluent. The first 400 ml. of eluate was discarded and a fraction (900 ml.) then collected was evaporated to give an oil. This oil (1.1 g.) and palladium on charcoal catalyst (1 g., 10%) in p-cymene (60 ml.) were heated under reflux for 30 minutes, cooled and filtered. The filtrate was shaken with 2N hydrochloric acid (3 × 25 ml.) and the aqueous acid solution was separated and neutralised by addition of potassium carbonate. The mixture was extracted with ethyl acetate and the extracts were dried over magnesium sulphate, filtered and evaporated. The residue in ether was treated with a solution of hydrogen chloride in anhydrous ether. The solid crystallised from a mixture of ethyl acetate and ether to give the product, m.p. 83°-84°.

Provenance & Evidence