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ChemicalBook CAS DataBase List 3-AMINO-6-METHOXYPYRIDAZINE
7252-84-8

3-AMINO-6-METHOXYPYRIDAZINE synthesis

2synthesis methods
A total of 3.40 g. (0.026 mol) 3-amino-6-chloropyridazine was placed in a Carius tube with a solution of sodium methoxide in methanol [prepared from 0.61 g. (0.027 mol) of clean sodium metal and 50 ml. of methanol], and the Carius tube was sealed. The tube was placed in a Carius furnace for 20 hours. After the tube was cooled and opened, the contents were removed, and the light brown solid was filtered off. The filtrate was evaporated to dryness at room temperature under an air jet. The resulting orange-brown crystalline solid was dissolved in a 60:40 petroleum ether-chloroform solution, treated with activated charcoal and filtered. There was obtained, upon. Talline solid fromn-amyl chloride accompanied by treat- 3 ment with activated charcoal yielded 0.51 g. of a white, crystalline solid 3-amino-6-methoxypyridazine melting at 103-105 ℃.
-

Yield:7252-84-8 85.7%

Reaction Conditions:

with copper in methanol at 160; for 24 h;

Steps:

15; 125.a (6-METHOXY-PYRIDAZIN-3-YL)- (2-METHYL-QUINAZOLIN-4-YL)-METHYL-AMINE; Scheme 15
3-Amino-6-methoxy-pyridazine: A mixture of 3-amino-6-chloro- pyridazin (500 mg, 3.86 MMOL), sodium methoxide (1.0 ml, 4.4 mmol, 25 % w/w) and copper powder (331 mg, 5.17 mmol) in methanol (3 ml) was heated in a sealed tube at 160 °C for 24 h. After cooling, the reaction mixture was diluted with methanol (10 ml) and filtered, and the filtrate was concentrated by vacuum. The residue was purified by chromatography on silica gel with acetate and hexane (1: 2) as eluent, yielding 413 mg of title compound (85.7 %). H NMR (CDC13) : 6.81 (M, 2H), 4.62 (brs, 2H), 4.00 (s, 3H).

References:

MYRIAD GENETICS, INC.;CYTOVIA, INC. WO2005/3100, 2005, A2 Location in patent:Page 135; 224-225

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