N-[4-(2,2-dicyanoethenyl)phenyl]acetamide

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

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

Procedure: 19 g (0.09 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 5.95 g (0.09 mol) of malononitrile and 9.91 g (0.09 mol) of thiophenol are initially charged in 120 ml of ethanol, and 0.4 ml of triethylamine are added. The mixture is stirred at reflux for 2 h, during which the product crystallizes. After cooling, the product is filtered off with suction and dried under reduced pressure. at reflux for 2 h, during which the product crystallizes After cooling the product is filtered off with suction dried under reduced pressure

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

Procedure: 32.6 g (0.2 mol) of 4-acetaminobenzaldehyde and 13.74 g (0.208 mol) of malononitrile are initially charged in 140 ml of ethanol, and 24 drops of piperidine are added. The mixture is stirred at reflux for 30 min. After cooling, the crystals are filtered off with suction and dried. at reflux for 30 min After cooling the crystals are filtered off with suction dried

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

Procedure: 32.6 g (0.2 mol) of 4-acetaminobenzaldehyde and 13.74 g (0.208 mol) of malononitrile are initially charged in 140 ml of ethanol, and 24 drops of piperidine are added. The mixture is stirred at reflux for 30 min. After cooling, the crystals are filtered off with suction and dried. at reflux for 30 min After cooling the crystals are filtered off with suction dried

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

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

Procedure: 318 g (1.5 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 99 g (1.5 mol) of malonitrile and 166 g (1.5 mol) of thiophenol are initially introduced in 2 000 ml of ethanol, and 6.7 ml of triethylamine are then added. The mixture is stirred under reflux for 2 hours, in connection with which crystallization takes place. After the mixture has cooled down to room temperature, the product is filtered off with suction and dried in vacuo. are then added under reflux for 2 hours, in connection with which crystallization the product is filtered off with suction dried in vacuo

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

Procedure: 311.4 g (1.9 mol) of 4-acetaminobenzaldehyde and 131 g (1.99 mol) of malonitrile are initially introduced in 1 330 ml of ethanol, and 6 ml of piperidine are then added. The mixture is stirred under reflux for 30 minutes. After cooling down to room temperature, the crystals are filtered off with suction and dried. are then added under reflux for 30 minutes the crystals are filtered off with suction dried

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

Procedure: 19 g (0.09 mol) of N-[4-(2,2-dicyanovinyl)phenyl]acetamide, 5.95 g (0.09 mol) of malononitrile and 9.91 g (0.09 mol) of thiophenol are initially charged in 120 ml of ethanol, and 0.4 ml of triethylamine are added. The mixture is stirred at reflux for 2 h, during which the product crystallizes. After cooling, the product is filtered off with suction and dried under reduced pressure. at reflux for 2 h, during which the product crystallizes After cooling the product is filtered off with suction dried under reduced pressure

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

Procedure: 32.6 g (0.2 mol) of 4-acetaminobenzaldehyde and 13.74 g (0.208 mol) of malononitrile are initially charged in 140 ml of ethanol, and 24 drops of piperidine are added. The mixture is stirred at reflux for 30 min. After cooling, the crystals are filtered off with suction and dried. at reflux for 30 min After cooling the crystals are filtered off with suction dried

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

Procedure: The portion (4.56 g) was dissolved in 50 mL of ethanol, 1.72 g of thiourea was added to the solution, and the mixture was heated to reflux for 1 hour. Next, to the reaction solution added 20 mL of ethanol and the solution was cooled, and further 4.79 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide and 3 g of sodium bicarbonate were added thereto, and then the mixture was heated to reflux for 1.5 hours. After the reaction solution was allowed to cool, 2.02 g of NBS was added to the solution, and the mixture was heated to reflux for 30 minutes. After reaction solution was allowed to cool, furthermore diisopropyl ether was added thereto, and the inorganic material precipitated was filtrated off, then the filtrate was again concentrated and dissolved in ethanol. Saturated aqueous sodium bicarbonate was added to the solution and the resulting crystal was filtrated, washed with water and ethanol, and then dried under reduced pressure to give 3.2 g of N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide as a white powder. the mixture was heated to reflux for 1 hour the solution was cooled the mixture was heated to reflux for 1.5 hours to cool the mixture was heated to reflux for 30 minutes After reaction solution to cool the inorganic material precipitated was filtrated off the filtrate was again concentrated dissolved in ethanol Saturated aqueous sodium bicarbonate was added to the solution the resulting crystal was filtrated washed with water and ethanol dried under reduced pressure

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

Procedure: To 20 mL of absolute ethanol, 250 mg of metallic sodium was added in small portions. After dissolved completely, 760 mg of thiourea was added to the above solution, and the mixture was stirred at room temperature for 1 hour. To the reaction, 2.11 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide was added, and the mixture was heated to reflux for 3 hours. Then, the solvent was removed under reduced pressure from the reaction mixture, the residue was dissolved in 30 mL of water. In addition, the mixture was acidified by adding acetic acid in small portions, thereto 30 mL of ethyl acetate was added and then the solution was stirred overnight. Filtration of the precipitated material gave 1.2 g of N-[4-(6-amino-5-cyano-2-mercapto-2,3-dihydropyrimidin-4-yl)phenyl]acetamide as a white powder. After dissolved completely was added the mixture was heated to reflux for 3 hours Then, the solvent was removed under reduced pressure from the reaction mixture the residue was dissolved in 30 mL of water by adding acetic acid in small portions 30 mL of ethyl acetate was added the solution was stirred overnight Filtration of the precipitated material

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

Procedure: The portion (4.56 g) was dissolved in 50 mL of ethanol, 1.72 g of thiourea was added to the solution, and the mixture was heated to reflux for 1 hour. Next, to the reaction solution added 20 mL of ethanol and the solution was cooled, and further 4.79 g of N-[4-(2,2-dicyanovinyl)phenyl]acetamide and 3 g of sodium bicarbonate were added thereto, and then the mixture was heated to reflux for 1.5 hours. After the reaction solution was allowed to cool, 2.02 g of NBS was added to the solution, and the mixture was heated to reflux for 30 minutes. After reaction solution was allowed to cool, furthermore diisopropyl ether was added thereto, and the inorganic material precipitated was filtrated off, then the filtrate was again concentrated and dissolved in ethanol. Saturated aqueous sodium bicarbonate was added to the solution and the resulting crystal was filtrated, washed with water and ethanol, and then dried under reduced pressure to give 3.2 g of N-{4-[6-amino-5-cyano-2-(6-methylpyridin-2-ylmethylsulfanyl)pyrimidin-4-yl]phenyl}acetamide as a white powder. the mixture was heated to reflux for 1 hour the solution was cooled the mixture was heated to reflux for 1.5 hours to cool the mixture was heated to reflux for 30 minutes After reaction solution to cool the inorganic material precipitated was filtrated off the filtrate was again concentrated dissolved in ethanol Saturated aqueous sodium bicarbonate was added to the solution the resulting crystal was filtrated washed with water and ethanol dried under reduced pressure