Sodium Sulfate → Carbamic acid, [2-methyl-4-[[(2-methyl-4-pyridinyl)amino]carbonyl]-5-thiazolyl]-, 1,1-dimethylethyl ester

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Reaction Steps

A solution of 2-methyl-pyridin-4-ylamine (0.623 g, 5.77 mmol) in 20 ml dry dioxane was treated at 0° C. with trimethylaluminium (2M in hexane, 2.88 ml, 5.77 mmol). The mixture was stirred at room temperature for 1 h. 5-tert-Butoxycarbonylamino-2-methyl-thiazole-4-carboxylic acid ethyl ester (0.55 g, 1.92 mmol) was added and the reaction mixture was refluxed for 4 h. 1 ml water and 2 g sodium sulfate were sequentially added and filtered. The filtrate was evaporated and the residue purified by flash chromatography on silica gel with heptane/ethyl acetate 100:0→0:100 to yield [2-methyl-4-(2-methyl-pyridin-4-ylcarbamoyl)-thiazol-5-yl]-carbamic acid tert-butyl ester (0.555 g, 83%) as a light yellow solid, MS (ISP): m/e=349.5 (M+H+).

Provenance & Evidence