2-Methyl-3-butyn-2-ol → HCID 70394546, compound

Participants

Reaction Steps

5.52 g of 5,6-dihydro-7-iodo-5-methyl-4H-imidazo[1,5-a]thieno[3,2-f][1,4]diazepine-one in 30 ml of diethylamine was treated with 1.92 ml of 2-methyl-3-butyn-2-ol, 75 mg of bis-(triphenylphosphine)-palladium(II) chloride and 13 mg of copper(I) iodide. The mixture was stirred at reflux temperature for 2 hours. The reaction mixture was then evaporated in a vacuum. The residue was dissolved in dichloromethane and this solution was washed twice with water. After drying over sodium sulphate this solution was chromatographed through 300 g of silica gel. Unreacted starting material was first recovered with dichloromethane/ethanol mixtures 99:1, 98:2 and 97:3. There was then eluted with dichloromethane/ethanol mixtures 96:4 and 95:5 an oily substance which crystallized from ethyl acelate/diethyl ether. There was obtained 5,6-dihydro-7-(3-hydroxy-3-methyl-1-butynyl)-5-methyl-4H-imidazo[1,5-a]-thieno[3,2-f][1,4]diazepine-one of melting point 180°-181°.

Provenance & Evidence