benzylurea

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a suspension of 24.78 g (165 mmol) of benzylurea and 25 ml (165 mmol) of diethyl malonate in 84 ml of methanol, 40.2 ml (165 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 32.12 g (89.2%, white crystal) of the desired product. was added at room temperature by refluxing for 16 hours After the reaction mixture was cooled the solvent was distilled off After the residue was dissolved in water insoluble substances were filtered out by adding concentrated hydrochloric acid The resulting precipitate was collected by filtration washed with water and n-hexane-diethyl ether dried

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

Procedure: To a suspension of 22.53 g (150 mmol) of benzylurea and 30.34 g (150 mmol) of diethyl isopropylmalonate in 77 ml of methanol, 36.6 ml (150 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 34.96 g (89.5%, white crystal) of the desired product. was added at room temperature by refluxing for 16 hours After the reaction mixture was cooled the solvent was distilled off After the residue was dissolved in water insoluble substances were filtered out by adding concentrated hydrochloric acid The resulting precipitate was collected by filtration washed with water and n-hexane-diethyl ether dried

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

Procedure: To a suspension of 22.53 g (150 mmol) of benzylurea and 37.5 g (150 mmol) of diethyl benzylmalonate in 77 ml of methanol, 36.6 ml (150 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 48.35 g (quant., white crystal) of the desired product. was added at room temperature by refluxing for 16 hours After the reaction mixture was cooled the solvent was distilled off After the residue was dissolved in water insoluble substances were filtered out by adding concentrated hydrochloric acid The resulting precipitate was collected by filtration washed with water and n-hexane-diethyl ether dried

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

Procedure: To a suspension of 21.83 g (145 mmol) of benzylurea and 25 ml (145 mmol) of diethyl methylmalonate in 74 ml of methanol, 35.4 ml (145 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 30.11 g (84.8%, white crystal) of the desired product. was added at room temperature by refluxing for 16 hours After the reaction mixture was cooled the solvent was distilled off After the residue was dissolved in water insoluble substances were filtered out by adding concentrated hydrochloric acid The resulting precipitate was collected by filtration washed with water and n-hexane-diethyl ether dried

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

Procedure: To a suspension of 100 g (666 mmol) of benzylurea and 156.8 g (666 mmol) of diethyl phenylmalonate in 340 ml of methanol, 164 ml (666 mmol) of a 4.1M sodium methylate solution was added at room temperature, followed by refluxing for 16 hours. After the reaction mixture was cooled, the solvent was distilled off. After the residue was dissolved in water and insoluble substances were filtered out, the filtrate was adjusted to pH 3-4 by adding concentrated hydrochloric acid. The resulting precipitate was collected by filtration, washed with water and n-hexane-diethyl ether and dried to yield 163.23 g (83.3%, white crystal) of the desired product. was added at room temperature by refluxing for 16 hours After the reaction mixture was cooled the solvent was distilled off After the residue was dissolved in water insoluble substances were filtered out by adding concentrated hydrochloric acid The resulting precipitate was collected by filtration washed with water and n-hexane-diethyl ether dried

Conditions: temp:5.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of-sodium methoxide (0.343 g, 14.9 mmol), benzylurea (1.6 g, 10.6 mmol), diethyl dimethylmalonate (1.9 g, 10 mmol) and methanol (15 mL) was heated 6 hours at reflux. The reaction mixture was concentrated and the residue was stirred with water (30 mL) at 5° C. and then hydrochloric acid was added. The solids were collected, washed with water and dried to give 1-benzyl-5,5-dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione, m.p 136°-137° C. was heated 6 hours at reflux The reaction mixture was concentrated hydrochloric acid was added The solids were collected washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), benzylurea (225 mg, 1.5 mmol, 1.5 equiv), 2-bromoanisole (125 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylendiamine (22 μL, 0.20 mmol, 0.20 equiv) and dry dioxane (1.0 mL), filled with nitrogen. The test tube was sealed and the reaction mixture was stirred at 80° C. for 26 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with ethyl acetate. The filtrate was concentrated in vacuo. The solid residue was dissolved in ˜2 mL DMF. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 2:1) provided 172 mg (67% yield) of the title compound as a white solid. filled with nitrogen The test tube was sealed The resulting suspension was cooled to room temperature filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate The filtrate was concentrated in vacuo The solid residue was dissolved in ˜2 mL DMF Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 2:1)

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

Procedure: A test tube was charged with CuI (20 mg, 0.10 mmol, 0.10 equiv), K3PO4 (425 mg, 2.0 mmol, 2.0 equiv), benzylurea (225 mg, 1.5 mmol, 1.5 equiv), 3-bromoaniline (109 μL, 1.0 mmol, 1.0 equiv), N,N′-dimethylethylendiamine (22 μL, 0.20 mmol, 0.20 equiv) and dry dioxane (1.0 mL), filled with nitrogen. The test tube was sealed and the reaction mixture was stirred at 80° C. for 24 h. The resulting suspension was cooled to room temperature and filtered through a 0.5×1 cm pad of silica gel, eluting with ethyl acetate. The filtrate was concentrated in vacuo. The solid residue was dissolved in ˜2 mL DMF. Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2) provided 185 mg (77% yield) of the title compound as a light yellow solid. filled with nitrogen The test tube was sealed The resulting suspension was cooled to room temperature filtered through a 0.5×1 cm pad of silica gel eluting with ethyl acetate The filtrate was concentrated in vacuo The solid residue was dissolved in ˜2 mL DMF Purification of the residue by flash chromatography on silica gel (2×20 cm; hexane:ethyl acetate 1:2)