2-amino-3-methyl-4H-imidazol-5-one

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 2.5 g (22.5 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 2.87 g (18 mM) of 5-chloro-2-thienyl isocyanate in 15 ml of toluene. The resulting mixture was heated at 80° C. for 3.5 hrs., cooled, and poured into a mixture of 250 ml of water and 50 ml of toluene. The precipitate was collected and recrystallized from ethyl acetate to give 1.5 g of the above urea as a tan solid, m.p. 204°-205° C. , cooled The precipitate was collected recrystallized from ethyl acetate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 2.5 g (22.5 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 2.87 g (18 mM) of 2-chloro-4-thienyl isocyanate in 20 mls toluene. The resulting mixture was heated at 80° C. for 3.5 hrs., cooled, and poured into a mixture of 250 ml of water and 50 ml toluene. The precipitate was collected and recrystallized from ethyl acetate to give 1.5 g of the above urea as a tan solid, m.p. 198°-200° C. , cooled The precipitate was collected recrystallized from ethyl acetate

Conditions: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 2.5 g (22.5 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 2.87 g (18 mM) of 2-chloro-4-thienyl isocyanate in 20 mls toluene. The resulting mixture was heated at 80° C. for 3.5 hrs., cooled, and poured into a mixture of 250 ml of water and 50 ml toluene. The precipitate was collected and recrystallized from ethyl acetate to give 1.5 g of the above urea as a tan solid, m.p. 198°-200° C. , cooled The precipitate was collected recrystallized from ethyl acetate

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 0.8 g (7.1 mM) of creatinine in 10 ml of anhydrous DMF was added a solution of 1.12 g (5.5 mM) of 3-bromo-2-thienyl isocyanate in 5 ml of toluene. The resulting mixture was heated at 65° C. for 5 hrs. (hours), cooled, and poured into a mixture of 200 ml water and 25 ml toluene. The precipitate was collected and recrystallized from ethyl acetate to give 0.36 g of the above urea as a tan colored solid, m.p. 192°-193° C. (dec.) (hours), cooled The precipitate was collected recrystallized from ethyl acetate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 18.3 g (162 mM) of creatinine in 120 ml of anhydrous DMF was added a solution of 17.2 g (162 mM) of 3-furanyl isocyanate in 80 ml of toluene. After stirring the mixture for 3 hrs. at 65° C., the mixture was partially concentrated under vacuum and the residue poured into 1200 ml of water. The resulting precipitate was collected, washed with water and recrystallized from ethyl acetate. The solid was then chromatographed over silica gel using ethyl acetate as the eluant and the fractions containing the product were concentrated and the residue recrystallized from toluene to give 0.5 g of the above urea as a tan solid, m.p. 179°-181° C. (dec.). at 65° C., the mixture was partially concentrated under vacuum the residue poured into 1200 ml of water The resulting precipitate was collected washed with water recrystallized from ethyl acetate The solid was then chromatographed over silica gel the fractions containing the product were concentrated the residue recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 18.3 g (162 mM) of creatinine in 120 ml of anhydrous DMF was added a solution of 17.2 g (162 mM) of 3-furanyl isocyanate in 80 ml of toluene. After stirring the mixture for 3 hrs. at 65° C., the mixture was partially concentrated under vacuum and the residue poured into 1200 ml of water. The resulting precipitate was collected, washed with water and recrystallized from ethyl acetate. The solid was then chromatographed over silica gel using ethyl acetate as the eluant and the fractions containing the product were concentrated and the residue recrystallized from toluene to give 0.5 g of the above urea as a tan solid, m.p. 179°-181° C. (dec.). at 65° C., the mixture was partially concentrated under vacuum the residue poured into 1200 ml of water The resulting precipitate was collected washed with water recrystallized from ethyl acetate The solid was then chromatographed over silica gel the fractions containing the product were concentrated the residue recrystallized from toluene

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred mixture of 6.9 g (60 mM) of creatinine in 100 ml of anhydrous DMF was added a solution of 6.5 g (60 mM) of 2-furanyl isocyanate in 75 ml of toluene. After stirring the mixture 1 hr. at 25° C. and then 1 hr. at 55° C., the solvents were removed in vacuo and the residue taken up in ethyl acetate and washed with water. The solvent was removed and the residue chromatographed over silica gel using ether-ethyl acetate (4:1) as the eluant. The fractions containing the product were combined and concentrated to leave 1.1 g of the above urea as an off-white solid, m.p. 173°-175° C. (dec.) at 25° C. 1 hr at 55° C., the solvents were removed in vacuo washed with water The solvent was removed the residue chromatographed over silica gel The fractions containing the product concentrated

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.0 g (26 mM) of creatinine in 25 ml of anhydrous DMF was added a solution of 4.1 g (26 mM) of 5-methoxy-2-thienyl isocyanate in 20 ml of toluene. The resulting mixture was heated at 65° C. for 4.5 hrs., cooled, and poured into 200 ml of water. The mixture was extracted with ethyl acetate, and the combined extracts dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate and then ethanol. Final purification was accomplished by chromatography over silica gel (ethyl acetate as eluant), decolorizing the product with charcoal, concentration and recrystallization from acetone-hexane to give 0.23 g of the above urea as a light brown solid, m.p. 180°-182° C. (dec.). , cooled The mixture was extracted with ethyl acetate the combined extracts dried (MgSO4) concentrated The residue was recrystallized from ethyl acetate Final purification with charcoal, concentration and recrystallization from acetone-hexane

Conditions: temp:65.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.0 g (26 mM) of creatinine in 25 ml of anhydrous DMF was added a solution of 4.1 g (26 mM) of 5-methoxy-2-thienyl isocyanate in 20 ml of toluene. The resulting mixture was heated at 65° C. for 4.5 hrs., cooled, and poured into 200 ml of water. The mixture was extracted with ethyl acetate, and the combined extracts dried (MgSO4) and concentrated. The residue was recrystallized from ethyl acetate and then ethanol. Final purification was accomplished by chromatography over silica gel (ethyl acetate as eluant), decolorizing the product with charcoal, concentration and recrystallization from acetone-hexane to give 0.23 g of the above urea as a light brown solid, m.p. 180°-182° C. (dec.). , cooled The mixture was extracted with ethyl acetate the combined extracts dried (MgSO4) concentrated The residue was recrystallized from ethyl acetate Final purification with charcoal, concentration and recrystallization from acetone-hexane

Conditions: temp:75.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.0 g (26 mM) of creatinine in 30 ml of anhydrous DMF was added a solution of 5.0 g (26.5 mM) of 5-bromo-2-thienyl isocyanate in 15 ml of toluene. The resulting mixture was heated at 75° C. for 3 hrs., cooled, and poured into 200 ml of water. The precipitate was collected, washed with ethanol and ether, and air-dried. The solid was dissolved in 250 ml hot acetone, treated with charcoal, filtered, and the filtrate diluted with water (250 ml). The resulting precipitate was collected, washed with acetone and then ether. Air-drying gave 2.3 g of the above urea as a buff powder, m.p. 192°-193° C. (dec.). , cooled The precipitate was collected washed with ethanol and ether air-dried The solid was dissolved in 250 ml hot acetone treated with charcoal filtered the filtrate diluted with water (250 ml) The resulting precipitate was collected washed with acetone Air-drying

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.0 g (26.0 mM) of creatinine in 50 ml of anhydrous DMF was added dropwise a solution of 3.7 g (26 mM) of 3-methyl-2-thienyl isocyanate in 35 ml of toluene. After stirring at 90° C. for 6 hrs., the reaction mixture was cooled and poured into 100 ml of water. The separated solid was collected, washed with water and recrystallized from ethyl acetate to give 1.2 g of the above urea as a grey-white solid, m.p. 201°-202° C. , the reaction mixture was cooled The separated solid was collected washed with water recrystallized from ethyl acetate

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a stirred suspension of 3.0 g (26.0 mM) of creatinine in 50 ml of anhydrous DMF was added dropwise a solution of 3.7 g (26 mM) of 3-methyl-2-thienyl isocyanate in 35 ml of toluene. After stirring at 90° C. for 6 hrs., the reaction mixture was cooled and poured into 100 ml of water. The separated solid was collected, washed with water and recrystallized from ethyl acetate to give 1.2 g of the above urea as a grey-white solid, m.p. 201°-202° C. , the reaction mixture was cooled The separated solid was collected washed with water recrystallized from ethyl acetate