Sodium Hydroxide → 6-(3-Amino-4-methylphenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole

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A mixture of 6-(4-methyl-3-nitrophenyl)-3-(3,4,5-trimethoxyphenyl)-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazole (256 mg, 0.6 mmol) and tin(II) chloride (675 mg, 3 mmol) in methanol (25 mL) was refluxed under argon for 6 h. It was then diluted with water (30 mL) and neutralized with 2N aqueous sodium hydroxide to pH=12, and extracted with ethyl acetate (3×20 mL). The extracts were dried, concentrated and the residue was purified by column chromatography (EtOAc as eluent) to give 66 mg (28%) of the title compound as solid. 1H NMR (CDCl3): 7.71 (s, 2H), 7.23 (m, 2H), 7.17 (s, 1H), 4.00 (s, 6H), 3.94 (s, 3H), 2.26 (s, 3H).

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