3-Methoxypyridazine

3-Methoxypyridazine3-chloro-6-methoxypyridazine (3.60 g, 24.90 mmol), 10percent Pd/C (1.590 g, 1.49 mmol) and ammonium formate (3.14 g, 49.81 mmol) were stirred in methanol (20 mL) at room temperature for thirty minutes. The reaction mixture was filtered through Celite to get rid of Pd/C, and the filtrate was evaporated to dry. The residue was dissolved in methylene chloride, washed with water once, dried through MgSOA mixture of 3-chloro-6-methoxypyridazine (1.0 g, 6.9 mmol) in methanol (50 mL) with 33percent palladium on carbon (100 mg) was hydrogenated under 45 psi overnight. The catalyst was removed by filtration through a pad of Celite. The filtrate was concentrated and dissolved in EtOAc. The solution was washed several times with a saturated NaHCOPREPARATION 8; 3- ethoxy-4-(tributylstannyl)pyridazine a) 3-MethoxypyridazinePalladium on carbon (10percent, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 °C for 1 hour. The reaction was cooled down, filtered through CelitePREPARATION 8 ;3-Methoxy-4-(tributylstannyl)pyridazine a) 3-Methoxypyridazine Palladium on carbon (10percent, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 C for 1 hour. The reaction was cooled down, filtered through Celite1) 3-Methoxypyridazine3-chloro-6-methoxypyridazine (3.60 g, 24.90 mmol), 10% Pd/C (1.590 g, 1.49 mmol) and ammonium formate (3.14 g, 49.81 mmol) were stirred in methanol (20 mL) at room temperature for thirty minutes. The reaction mixture was filtered through Celite to get rid of Pd/C, and the filtrate was evaporated to dry. The residue was dissolved in methylene chloride, washed with water once, dried through MgSO4, filtrated and evaporated to dry to give a brown liquid as the title compound (2.41 g, 88% yield, 95% purity). The crude material was used for next step without further purification. 1H NMR (300 MHz, CHLOROFORM-d) delta ppm 8.83 (dd, J=4.4, 1.3 Hz, 1 H) 7.35 (dd, J=8.9, 4.4 Hz, 1 H) 6.97 (dd, J=8.9, 1.3 Hz, 1 H) 4.14 (s, 3 H. MS APCI, m/z=152 (M+ACN+H). HPLC 0.43 min.A mixture of 3-chloro-6-methoxypyridazine (1.0 g, 6.9 mmol) in methanol (50 mL) with 33% palladium on carbon (100 mg) was hydrogenated under 45 psi overnight. The catalyst was removed by filtration through a pad of Celite. The filtrate was concentrated and dissolved in EtOAc. The solution was washed several times with a saturated NaHCO3 solution and brine, dried over MgSO4, concentrated to give a crude product, which was purified on a silica gel column eluting with EtOAc/n-hexane (1:2) to give PREPARATION 8; 3- ethoxy-4-(tributylstannyl)pyridazine a) 3-MethoxypyridazinePalladium on carbon (10%, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 C for 1 hour. The reaction was cooled down, filtered through Celite under nitrogen atmosphere eluting with methanol and the filtrate was evaporated to dryness. The crude product was diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (1.55 g, 86%) as a pale yellow oil.1H-NMR delta (300 MHz, CDCI3): 4.16 (s, 3H), 7.00 (dd, 1 H), 7.38 (dd, 1 H), 8.82 -8.87 (m, 1H).PREPARATION 8 ;3-Methoxy-4-(tributylstannyl)pyridazine a) 3-Methoxypyridazine Palladium on carbon (10%, 0.1 g) and ammonium formate (2.1 g, 33.3 mmol) were added to a stirred solution of 3-chloro-6-methoxypyridazine (2.5 g, 26.43 mmol) in methanol (10 mL) and the resulting mixture was stirred at 50 ºC for 1 hour. The reaction was cooled down, filtered through Celite under nitrogen atmosphere eluting with methanol and the filtrate was evaporated to dryness. The crude product was diluted with dichloromethane and washed with water. The organic layer was dried over magnesium sulphate and the solvent removed under reduced pressure to yield the title compound (1.55 g, 86%) as a pale yellow oil. 1H-NMR delta (300 MHz, CDCl3): 4.16 (s, 3H), 7.00 (dd, 1H), 7.38 (dd, 1H), 8.82 - 8.87 (m, 1H).1) 3-Methoxypyridazine In a hydrogen atmosphere, at room temperature, 10% palladium-carbon (wet. 3.12 g) was added to a solution of 3-chloro-6-methoxypyridazine (30.0 g) in methanol (200 mL), and the mixture was stirred for 17 hours. The reaction mixture was subjected to filtration, and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified through silica gel column chromatography (ethyl acetate), to thereby give

Molecular Weight:110.11
XLogP3:0.1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:110.048012819
Monoisotopic Mass:110.048012819
Topological Polar Surface Area:35
Heavy Atom Count:8
Complexity:67.4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes