Dimethylformamide → HCID 22335225, compound

Participants

Reaction Conditions

Reaction Steps

n-Butyllithium (1.6M in hexane, 9 ml, 14.4 mmol) was added to the imidazopyrazine from preparation 79 (2.8 g, 13.13 mmol) in tetrahydrofuran (20 ml) under a nitrogen atmosphere at −78° C. at a rate that maintained the reaction temperature below −70° C. The mixture was warmed to 0° C. and was stirred for 10 minutes and then cooled to −78° C. N,N-Dimethylformamide (1.5 ml, 19.4 mmol) was added dropwise and the mixture was warmed to 0° C. and was stirred for 10 minutes. Saturated sodium hydrogen carbonate solution (40 ml), then water (100 ml) were added and the aqueous solution was extracted with ethyl acetate (100 ml). The organic solution was washed with water (50 ml), then brine (50 ml), dried over magnesium sulphate and evaporated under reduced pressure. The residue was purified by chromatography on silica gel using ethyl acetate in pentane as eluant (gradient from 70:30 to 90:10) to give the title compound as a yellow solid (2.67 g).

Provenance & Evidence