Potassium Hydroxide → HCID 86736887, compound

Participants

Reaction Steps

To a solution of 1.80 parts by weight of 2,3-pyrazinedicarboximide which was prepared according to the procedure described in Helvetica Chemica Acta 41 (1958) p. 512 in 40 parts by volume of dry dimethylformamide is added 17.0 parts by volume of methanol containing 0.85 parts by weight of potassium hydroxide pellets. The combination of these two solutions results in the formation of a precipitate. To this mixture is then added in one portion a slightly warm solution of 3.01 parts by weight of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazole methanesulfonate (preparation of 1-(2-hydroxyethyl)-2-methyl-5-nitroimidazolemethanesulfonate is described in U.S. Pat. No. 3,770,763) in 40.0 parts by volume of dimethylformamide. The mixture turns dark blue in color, then upon swirling turns green in color and eventually turns yellow in color. The mixture is then heated on a steam bath for 4 hours at an internal temperature of 70°-85° C. After cooling, the mixture to room temperature the insoluble material is separated by filtration, rinsed with dimethylformamide and air dried. The mother liquor is rinsed into a round bottom flask, concentrated to a volume of about 40 parts, then diluted to a volume of 100 parts with water and allowed to stand overnight. The resulting solid material which separates out of this liquor is separated by filtration, washed with water and air dried to afford a product, in the form of brown needles, melting at 231°-234° C. This product is then taken up in 8.0 parts by volume of warm dimethylformamide; activated carbon is added to the solution and the solution is then filtered. The filtrate is diluted with 20 parts by volume of water and then seeded. The resulting crystals are separated by filtration, washed with methanol and air dried to afford 6-[2-(2-methyl-5-nitro-1H-imidazole-1-yl)ethyl]-5H-pyrrolo[3,4-b]pyrazine-5,7(6H-dione), melting at 232°-234° C. This compound is represented by the following structural formula ##STR7##

Provenance & Evidence