Dimethylamine → (4-Dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

2-Amino-thiazole-4-carboxylic acid dimethylamide was prepared as follows. (1) A solution of 2-tert-butoxycarbonylamino-thiazole-4-carboxylic acid (0.5 g, 2 mmol) (prepared as described in Examples 4a and 4b) in thionyl chloride (10 mL) was heated at reflux (80° C.) for 2 hours. The reaction mixture was then concentrated under reduced pressure. To the residue was added a 2 M solution of dimethylamine in tetrahydrofuran (10 mL, 20 mmol) and methanol (10 mL). The reaction mixture was stirred at room temperature for 20 hours and concentrated. The residue was purified by chromatography over silica gel eluted with 2:1 ethyl acetate/hexanes to give (4-dimethylcarbamoyl-thiazol-2-yl)-carbamic acid tert-butyl ester as a yellow foam (0.26 g, 48%).

Provenance & Evidence