With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.1632-76-4,3-Methylpyridazine,as a common compound, the synthetic route is as follows.
A solution of 3-Methylpyridazine 15 (5.0 g, 53.0 mmol) in THF (10 mL) was added to potassium tert-butoxide (8.9 g, 80.0 mmol) in THF (50 mL) at 0 C. After stirring at room temperature for 1.5 hours, tert-butyl nitrite (12.6 mL, 106 mmol) in THF (10 mL) was added to the reaction mixture at 0 C. After stirring at room temperature for 19 hours, the solvent was removed in vacuo and the residue was added to 4 M HCl solution (20 mL). The resulting mixture was concentrated in vacuo and filtered a colorless powder of aldoxime 16a (1.8 g). The residue was extracted with ethylacetate (50 mL 3). The organic layer was dried over MgSO4. The solvent was removed in vacuo, then triturated with n-hexane to yield aldoxime 16a (2.8 g). The combined aldoxime 16a (4.6 g, 71%) was E, Z mixture of isomer. N-Chlorosuccimide (4.0g, 30 mmol) was added to a suspension of 16a (3.7 g, 30 mmol), ethynyl tri-n-butylstannane (9.3 g, 20 mmol), NaHCO3 (6.3 g, 75 mmol), ethyacetate (100 mL) and distilled water (5 mL). After stirring at room temperature for 16 hours, distilled water (5 mL) was added to the reaction mixture. After stirring at room temperature for 4 hours, the reaction mixture was washed with saturated NaHCO3 (100 mL), and the aqueous layer was extracted with ethylacetate (100 mL). The combined organic layer was dried over MgSO4. The solvent was removed in vacuo and the residue was used in the next reaction without further purification. The crude 17a was dissolved in THF (100 mL). Iodine (3.2 g, 25.2 mmol) was added to the solution at room temperature. After stirring at room temperature for 35 minutes, the reaction mixture was diluted with 6% sodium thiosulfate solution (100 mL) and extracted with ethylacetate (100 ml). The organic layer was washed with brine and dried over MgSO4. The solvent was removed in vacuo and the residue was recrystallized from n-hexane to yield compound 14a (2.9 g, 35% for two steps) as a brown powder
1632-76-4 3-Methylpyridazine 74208, apyridazine compound, is more and more widely used in various.
Reference£º
Article; Sugimoto, Tomohiro; Shimazaki, Yoichi; Manaka, Akira; Tanikawa, Tetsuya; Suzuki, Keiko; Nanaumi, Kayoko; Kaneda, Yoshie; Yamasaki, Yukiko; Sugiyama, Hiroyuki; Bioorganic and Medicinal Chemistry Letters; vol. 22; 17; (2012); p. 5739 – 5743;,
Pyridazine – Wikipedia
Pyridazine | C4H4N2 – PubChem