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Preparation 5 Synthesis of 3-methoxy-4,5-dimethyl-6-chloropyridazine 0.46 g(0.02 mol) of metallic sodium was dissolved in 30 ml of absolute methanol and then 3.54 g(0.02 mol) of 3,6-dichloro-4,5-dimethylpyridazine obtained from Preparation 3 was added thereto and completely dissolved. The reaction solution was stirred for one hour at room temperature and concentrated under reduced pressure to remove excessive methanol. 100 ml of diethyl ether was added to the residue and then vigorously stirred for 10 minutes. The diethyl ether-insoluble materials were removed off and the remaining solution was washed two times with 50 ml of purified water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to remove diethyl ether. In this manner, the title compound was obtained as a white needle crystal. Yield: 2.63 g (76.2percent) Melting Point: 80-82° C. Recrystallizing solvent: ethanol
Preparation 5 Synthesis of 3-methoxy-4,5-dimethyl-6-chloropyridazine 0.46g(0.02mol) of metallic sodium was dissolved in 30mlitre of absolute methanol and then 3.54g(0.02mol) of 3,6-dichloro-4,5-dimethylpyridazine obtained from Preparation 3 was added thereto and completely dissolved. The reaction solution was stirred for one hour at room temperature and concentrated under reduced pressure to remove excessive methanol. 100mlitre of diethyl ether was added to the residue and then vigorously stirred for 10 minutes. The diethyl ether-insoluble materials were removed off and the remaining solution was washed two times with 50mlitre of purified water, dried over anhydrous sodium sulfate and then concentrated under reduced pressure to remove diethyl ether. In this manner, the title compound was obtained as a white needle crystal, Yield: 2.63g (76.2percent) Melting Point: 80-82°C Recrystallizing solvent: ethanol
9
[ 34584-69-5 ]
3-methoxy-4,5-dimethyl-6-chloropyridazine[ No CAS ]
3-ethoxy-4,5-dimethyl-6-chloropyridazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
In ethanol;
Preparation 8 Synthesis of 3-ethoxy-4,5-dimethyl-6-chloropyridazine 0.69 g(0.03 mol) of metallic sodium was dissolved in 100 ml of absolute ethanol and then 5.31 g(0.03 mol) of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> was added thereto and completely dissolved. The reaction solution was stirred for 4 hours at room temperature and then treated according to the same manner as Preparation 5 to obtain the title compound as a pale white crystal. Yield: 4.22 g (75.4percent) Melting Point: 60-62° C. Recrystallizing solvent: ethanol NMR(CDCl3, delta): 1.42(t, 3H, CH3), 2.20((s, 3H, CH3), 2.32(s, 3H, CH3), 4.52(q, 2H, OCH2)
In ethanol;
Preparation 8 Synthesis of 3-ethoxy-4,5-dimethyl-6-chloropyridazine 0.69g(0.03mol) of metallic sodium was dissolved in 100mlitre of absolute ethanol and then 5.31g(0.03mol) of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong> was added thereto and completely dissolved. The reaction solution was stirred for 4 hours at room temperature and then treated according to the same manner as Preparation 5 to obtain the title compound as a pale white crystal. Yield: 4.22g (75.4percent) Melting Point: 60-62°C Recrystallizing solvent: ethanol NMR(CDCl3, delta): 1.42(t, 3H, CH3), 2.20((s, 3H, CH3), 2.32(s, 3H, CH3), 4.52(q, 2H, OCH2)
3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
2 parts (30%)
With potassium carbonate; In water;
Example 36 A mixture of 3.9 parts of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong>, 4.2 parts of 1-(2,3-dimethylphenyl)piperazine and 2.94 parts of potassium carbonate was stirred and heated for 4 hours in an oil bath at 190° C. After cooling, the mixture was taken up in water and trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2 parts (30percent) of 3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine; mp. 194.5° C. (compound 217).
2 parts (30%)
With potassium carbonate; In water;
Example 36 A mixture of 3.9 parts of <strong>[34584-69-5]3,6-dichloro-4,5-dimethylpyridazine</strong>, 4.2 parts of 1-(2,3-dimethylphenyl)piperazine and 2.94 parts of potassium carbonate was stirred and heated for 4 hours in an oil bath at 190°C. After cooling, the mixture was taken up in water and trichloromethane. The organic layer was separated, dried, filtered and evaporated. The residue was crystallized from 2-propanol. The product was filtered off and dried, yielding 2 parts (30percent) of 3-chloro-6-[4-(2,3-dimethylphenyl)-1-piperazinyl]-4,5-dimethylpyridazine; mp. 194.5°C (compound 217).
Description 10; 3-Chloro-6-iodo-4,5-dimethyl-pyridazine (DlO); N - N A mixture of D9 (0.2 g, 1.13 mmol), sodium iodide (0.420 g, 2.8 mmol) and hydroiodic acid (57 wt.percent in water, 2 ml) was stirred at 120 0C for 10 min., under microwave irradiation. The mixture was then poured into an aqueous saturated solution of sodium carbonate, Na2S2O3, water and dichloromethane. The organic phase was separated, filtered over cotton, and the solvent evaporated in vacuo. The residue was purified by column chromatography (dichloromethane / heptane 1 :1 to 8:2) to yield DlO (0.235 g, 77percent) as a solid. C6H6CUN2 requires 268; Found 269 (MH+).
With N-ethyl-N,N-diisopropylamine; trichlorophosphate; at 160℃; for 0.333333h;Microwave irradiation;
Description 9; 3,6-Dichloro-4,5-dimethyl-pyridazine (D9); A mixture of 6-hydroxy-4,5-dimethyl-2H-pyridazin-3-one (2.56 g, 18 mmol) (prepared by a procedure similar to that described in WO 99/36407), phosphorus oxychloride (8 ml) and diisopropylethylamine (4 ml) was stirred at 160 0C for 20 min., under microwave irradiation (Biotage MW-oven). The solvent was then partially evaporated in vacuo and remaining material poured into a mixture of cold water, saturated sodium hydrogen carbonate and dichloromethane. The mixture was then basified with portions of sodium hydrogen carbonate until there was no more CO2 evolution. The organic layer was separated, dried (Na2SO4), filtered and the solvent evaporated in vacuo. The residue was purified by column chromatography (dichloromethane / heptane 1/1 to 10/0) to yield D9 (1.7 g, 53 percent) as a solid. C6H6Cl2N2 requires 176; Found 177 (MH+)
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