Water → HCID 13559525, compound

Participants

Reaction Steps

Under non-aqueous conditions 200 ml of a mixture of boron trichloride (0.2 mol) and methylene chloride (1 mol) is added over a period of 20 minutes with vigorous stirring to a solution containing 30 g of 5-chloro-8-(2-ethoxyethyl)-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine (0.1 moles) dissolved in 300 ml of chloroform. The resulting reaction mixture is stirred at room temperature for 3 hours. To the reaction mixture is added 400 ml of water and the resulting mixture is stirred for 1.5 hours and then allowed to stand at room temperature. The aqueous and organic layers are separated and the organic layer is dried over sodium sulfate, filtered and evaporated yielding a residue. The residue is chromatographed on silica gel and recrystallized from diethyl ether to yield 5-chloro-7-phenyl[1,2,4]triazolo[1,5-c]pyrimidine-8-ethanol having the structural formula ##STR21## and the azido tautomer thereof as a white solid having a melting point of 104°-105° C. and the following elemental analysis:

Provenance & Evidence