(2E)-1-(4-氯苯基)-3-(二甲基氨基)-2-丙烯-1-酮

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Stage 3.05 g (3.23 mmol) of 4-chloroacetophenone are stirred in 3.6 ml of dimethylformamide diethylacetal for 17.5 h at 110°. After cooling, precipitation is effected with hexane and the precipitate is isolated by filtration and dried. 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one is obtained; 1H-NMR (DMSO): 2.9 (3H,s), 3.1 (3H,s), 5.8 (1H,d), 7.5 (2H,m), 7.75 (1H,d), 7.95 (2H,m). After cooling precipitation the precipitate is isolated by filtration dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 539 mg (2.15 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 450 mg (2.15 mmol) of 3-dimethylamino-1-(4-chloro-phenyl)-2-propen-1-one in 5.5 ml of 2-propanol. After the addition of 94.5 mg (2.36 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 29 h. After cooling to RT, the product is isolated by filtration and washed with 1-propanol and water. After drying at 60° under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(4-chloro-phenyl)-2-pyrimidineamine is obtained; Rf =0.45 (methylene chloride:methanol =98:2), MS: 397 (M+), m.p. 133°-135°. under reflux for 29 h the product is isolated by filtration washed with 1-propanol and water After drying at 60° under HV

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 539 mg (2.15 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 450 mg (2.15 mmol) of 3-dimethylamino-1-(4-chloro-phenyl)-2-propen-1-one in 5.5 ml of 2-propanol. After the addition of 94.5 mg (2.36 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 29 h. After cooling to RT, the product is isolated by filtration and washed with 1-propanol and water. After drying at 60° under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(4-chloro-phenyl)-2-pyrimidineamine is obtained; Rf =0.45 (methylene chloride:methanol =98:2), MS: 397 (M+), m.p. 133°-135°. under reflux for 29 h the product is isolated by filtration washed with 1-propanol and water After drying at 60° under HV

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: The title compound was prepared from crude 1-(4-chloro-phenyl)-3-dimethylamino-propenone (87 mg, 0.3 mmol) and N-[3-methoxy-4-(4-methyl-imidazol-1-yl)-phenyl]-guanidine dinitrate (83 mg, 0.22 mmol) using in analogous manner the procedure described in example 28b). Obtained as a pale-yellow solid (29 mg, 33%). Mp 202-204° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 1-(4-Chloro-phenyl)-ethanone (49 mg, 0.3 mmol) was reacted with tert.-butoxy-bis-(dimethylamino)-methane using in analogous manner the procedure described in example 28a) to give crude title compound (87 mg) as a yellow solid which was used directly in the next step.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: A mixture of 10.0 g. of p-chloroacetophenone and 25 ml. of dimethylformamide dimethylacetal is refluxed for 3 hours. Evaporation gives a thick oil which crystallized with the addition of hexane, to give the product, m.p. 78.5°-80.5° C. Recrystallization from methylene chloride and hexane provides the product of the Example as crystals, m.p. 83°-84° C. A mixture of 10.0 g Evaporation gives a thick oil which crystallized with the addition of hexane to give the product, m.p. 78.5°-80.5° C Recrystallization from methylene chloride and hexane provides the product of the Example as crystals, m.p. 83°-84° C.

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Stage 3.05 g (3.23 mmol) of 4-chloroacetophenone are stirred in 3.6 ml of dimethylformamide diethylacetal for 17.5 h at 110°. After cooling, precipitation is effected with hexane and the precipitate is isolated by filtration and dried. 3-dimethylamino-1(4-chloro-phenyl)-2-propen-1-one is obtained; 1H-NMR (DMSO): 2.9 (3H,s), 3.1 (3H,s), 5.8 (1H,d), 7.5 (2H,m), 7.75 (1H,d), 7.95 (2H,m). After cooling precipitation the precipitate is isolated by filtration dried

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 539 mg (2.15 mmol) of 3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl-guanidine nitrate are added to a solution of 450 mg (2.15 mmol) of 3-dimethylamino-1-(4-chloro-phenyl)-2-propen-1-one in 5.5 ml of 2-propanol. After the addition of 94.5 mg (2.36 mmol) of sodium hydroxide, the reaction mixture is boiled under reflux for 29 h. After cooling to RT, the product is isolated by filtration and washed with 1-propanol and water. After drying at 60° under HV, N-[3-(1,1,2,2-tetrafluoro-ethoxy)-phenyl]-4-(4-chloro-phenyl)-2-pyrimidineamine is obtained; Rf =0.45 (methylene chloride:methanol =98:2), MS: 397 (M+), m.p. 133°-135°. under reflux for 29 h the product is isolated by filtration washed with 1-propanol and water After drying at 60° under HV