1,3-diethylurea

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

Procedure: Acetic anhydride (16 ml, 0.15 mole) was added dropwise over two hours to a solution of 1,3-diethylurea (5.3 g, 0.05 mole) and malonic acid (5.2 g, 0.05 mole) in acetic acid (40 ml) at 65° C. After the addition was complete, the temperature was raised to 90° C. and maintained there for three hours. The solvent was evaporated under reduced pressure and the residue boiled with ethanol for fifteen minutes. After some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C. After the addition maintained there for three hours The solvent was evaporated under reduced pressure the residue boiled with ethanol for fifteen minutes After some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C.

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

Procedure: Acetic anhydride (16 ml, 0.15 mole) was added dropwise over two hours to a solution of 1,3-diethylurea (5.3 g, 0.05 mole) and malonic acid (5.2 g, 0.05 mole) in acetic acid (40 ml) at 65° C. After the addition was complete, the temperature was raised to 90° C. and maintained there for three hours. The solvent was evaporated under reduced pressure and the residue boiled with ethanol for fifteen minutes. After some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C. After the addition maintained there for three hours The solvent was evaporated under reduced pressure the residue boiled with ethanol for fifteen minutes After some time, 1,3-diethyl-2,4,6-(1H,3H,5H)- pyrimidinetrione crystallized in cubic crystals, m.p. 52° C.

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl veratroylacetate (10 g) and N,N'-diethylurea (5.06 g) were added conc.hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc.hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g). were added conc To the residue was added another conc extracted with ethyl acetate The extract was dried over magnesium sulfate evaporated under reduced pressure The residue was triturated with a mixture of diisopropyl ether and ethyl acetate

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl veratroylacetate (10 g) and N,N'-diethylurea (5.06 g) were added conc.hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc.hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g). were added conc To the residue was added another conc extracted with ethyl acetate The extract was dried over magnesium sulfate evaporated under reduced pressure The residue was triturated with a mixture of diisopropyl ether and ethyl acetate

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

Procedure: 12.69 grams (0.14 mol) of diethylurea and 11.90 grams (0.14 mol) of cyanoacetic acid were heated in acetic anhydride at 60° C. for 3 hours, under dry atmosphere. Thereafter, the acetic anhydride and remaining cyanoacetic acid were evaporated, 5% sodium hydroxide was added and the mixture was stirred and cooled. 20 grams of 6-amino-1,3-diethyluracil were obtained as a precipitate. 11.8 grams of sodium nitrite in 70 ml water were then added while cooling and stirring and the solution was then acidified by adding 70 ml acetic acid. The mixture was stirred at room temperature for additional 2.5 hours. The resulting precipitate was filtered, washed with water, ethanol and finally ether so afford 10.1 grams of 6-amino-1,3-diethyl-5-nitrosouracil, as a violet product. under dry atmosphere were evaporated 5% sodium hydroxide was added cooled

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl veratroylacetate (10 g) and N,N'-diethylurea (5.06 g) were added conc. hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc. hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g). the mixture was heated again at 120° C. for 4 hours under reduced pressure extracted with ethyl acetate The extract was dried over magnesium sulfate evaporated under reduced pressure The residue was triturated with a mixture of diisopropyl ether and ethyl acetate

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl veratroylacetate (10 g) and N,N'-diethylurea (5.06 g) were added conc. hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc. hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g). the mixture was heated again at 120° C. for 4 hours under reduced pressure extracted with ethyl acetate The extract was dried over magnesium sulfate evaporated under reduced pressure The residue was triturated with a mixture of diisopropyl ether and ethyl acetate

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

Procedure: 3.0 g of tert-butyl 3-{cyclohexyl[(diethyl-amino)carbonyl]amino}-8-azabicyclo[3.2.1]octane-8-carboxylate mixed with diethylurea are placed in 37 ml of 2N hydrochloric acid in diethyl ether. The reaction medium is stirred at ambient temperature for 16 h. After evaporation to dryness, the residue is taken up with a 1N aqueous hydrochloric acid solution. Extraction is carried out with ethyl acetate and a 1N aqueous sodium hydroxide solution is then added up to a pH of 10. Extraction is carried out with ethyl acetate until the aqueous phase is completely depleted. The organic phase is washed with H2O and then with a saturated aqueous sodium chloride solution. After drying over MgSO4 and concentration to dryness, 1.8 g of N-8-azabicyclo[3.2.1]oct-3-yl-N-cyclohexyl-N′,N′-diethylurea are obtained. After evaporation to dryness Extraction a 1N aqueous sodium hydroxide solution is then added up to a pH of 10 Extraction The organic phase is washed with H2O After drying over MgSO4 and concentration to dryness, 1.8 g of N-8-azabicyclo[3.2.1]oct-3-yl-N-cyclohexyl-N′,N′-diethylurea are obtained

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

Procedure: 12.69 grams (0.14 mol) of diethylurea and 11.90 grams (0.14 mol) of cyanoacetic acid were heated in acetic anhydride at 60° C. for 3 hours, under dry atmosphere. Thereafter, the acetic anhydride and remaining cyanoacetic acid were evaporated, 5% sodium hydroxide was added and the mixture was stirred and cooled. 20 grams of 6-amino-1,3-diethyluracil were obtained as a precipitate. 11.8 grams of sodium nitrite in 70 ml water were then added while cooling and stirring and the solution was then acidified by adding 70 ml acetic acid. The mixture was stirred at room temperature for additional 2.5 hours. The resulting precipitate was filtered, washed with water, ethanol and finally ether so afford 10.1 grams of 6-amino-1,3-diethyl-5-nitrosouracil, as a violet product. under dry atmosphere were evaporated 5% sodium hydroxide was added cooled

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

Procedure: 12.69 grams (0.14 mol) of diethylurea and 11.90 grams (0.14 mol) of cyanoacetic acid were heated in acetic anhydride at 60° C. for 3 hours, under dry atmosphere. Thereafter, the acetic anhydride and remaining cyanoacetic acid were evaporated, 5% sodium hydroxide was added and the mixture was stirred and cooled. 20 grams of 6-amino-1,3-diethyluracil were obtained as a precipitate. 11.8 grams of sodium nitrite in 70 ml water were then added while cooling and stirring and the solution was then acidified by adding 70 ml acetic acid. The mixture was stirred at room temperature for additional 2.5 hours. The resulting precipitate was filtered, washed with water, ethanol and finally ether so afford 10.1 grams of 6-amino-1,3-diethyl-5-nitrosouracil, as a violet product. under dry atmosphere were evaporated 5% sodium hydroxide was added cooled

Conditions: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 21.8 g (0.1 mol) of 4,5-dichloro-2-dichloromethyleneimidazole were added to a solution of 26 g (0.22 mol) of N,N'-diethylurea in 150 ml of water and the mixture was heated to 100° C. while stirring. After cooling, the product was filtered off, washed with water and dried. In this way, 18.5 g (66% of theory) of 4,5-dichloro-imidazol-2-oyl-N,N'-diethylurea with a melting point of 159° C. were obtained. After cooling the product was filtered off washed with water dried

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of ethyl veratroylacetate (10 g) and N,N'-diethylurea (5.06 g) were added conc.hydrochloric acid (1 drop) and ethanol (1 ml). The mixture was heated at 120° C. for 3.5 hours under reduced pressure. To the residue was added another conc.hydrochloric acid (2 drops) and the mixture was heated again at 120° C. for 4 hours under reduced pressure. To the reaction mixture was added water and extracted with ethyl acetate. The extract was dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated with a mixture of diisopropyl ether and ethyl acetate to give 1,3-diethyl-6-(3,4-dimethoxyphenyl)-2,4(1H,3H)-pyrimidinedione (3.20 g). were added conc To the residue was added another conc extracted with ethyl acetate The extract was dried over magnesium sulfate evaporated under reduced pressure The residue was triturated with a mixture of diisopropyl ether and ethyl acetate