Dimethylformamide → Hydrochloric Acid

Participants

Reaction Steps

To a slurry of 530 mg (22 mmol) of pentane-washed sodium hydride in 50 ml of dry dimethylformamide (DMF) was added 1.37 g (10.0 mmol) of 2-hydroxymethyl)-4,5-dihydroimidazole hydrochloride. After 30 minutes at room temperature, 1.55 g (10.0 mmol) of 8-chloroimidazo[1,2-a]pyrazine in 30 ml of DMF was added dropwise. After 1 hour at room temperature, the mixture was concentrated to dryness. The residue was dissolved in 30 ml of water and extracted with 2×50 ml of chloroform. The combined organic extracts were dried (Na2SO4), filtered, and concentrated. The oily residue was purified by flash chromatography (230-400 mesh SiO2 ; 10% MeOH/CHCl3 saturated with NH3 as eluent) to afford the product. Treatment with ethanolic HCl and excess diethyl ether afforded the crystalline dihydrochloride hemihydrate salt of the product, m.p. 162°-165° C. (dec).

Provenance & Evidence