ChemicalBook CAS DataBase List 6-chloro-2,8-dimethyl-Imidazo[1,2-b]pyridazine

6-chloro-2,8-dimethyl-Imidazo[1,2-b]pyridazine synthesis

4synthesis methods

Product Name:6-chloro-2,8-dimethyl-Imidazo[1,2-b]pyridazine
CAS Number:17412-23-6
Molecular formula:C8H8ClN3
Molecular Weight:181.62

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6-chloro-2,8-dimethyl-Imidazo[1,2-b]pyridazine

17412-23-6
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Yield:17412-23-6 54.6%

Reaction Conditions:

Stage #1:3-amino-6-chloro-4-methylpyridazine;1-bromoacetone in acetonitrile for 8 h;Heating / reflux;
Stage #2: with sodium hydroxide;water; pH=9

Steps:

62 Reference Example 62; Synthesis of 6-chloro-2,8-dimethylimidazo[1,2-b]pyridazine
3-Amino-6-chloro-4-methylpyridazine (5.50 g, 38.3 mmol) and bromoacetone (6.90 g, 40.0 mmol) were heated in acetonitrile (50.0 ml) for 8 hours under reflux. The reaction solution was concentrated under reduced pressure, and water (100 ml) was added to the residues which were then adjusted to pH 9 with 20% aqueous sodium hydroxide and extracted twice with ethyl acetate. The extracts were combined, dried over anhydrous magnesium sulfate and concentrated, and the residues were purified'by silica gel column chromatography (ethyl acetate : chloroform = 1 : 2), to give the title compound as white crystals. The yield was 3.80 g (54.6%). mp 109-110°C1H NMR (CDCl3, δ): 2.49-2.50(3H, m), 2.63-2.64(3H, m), 6.83-6.85(1H, m), 7.66(1H, s). IR(Nujol, cm-1): 3129, 1592, 1532, 1289, 1113, 1092, 985, 928, 843, 772.

References:

Sumitomo Chemical Takeda Agro Company, Limited EP1466527, 2004, A1 Location in patent:Page 36

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