Acetic Acid → HCID 57586385, compound

Participants

Reaction Steps

To a solution of 5-chloro-4-(4-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)phenyl)thiazol-2-amine (0.70 g, 2.0 mmol), prepared in the previous step, in THF (10 mL) at 0° C. was added acetic acid (0.125 mL, 2.2 mmol) and tetrabutylammonium fluoride (2.2 mL, 1 M in THF, 2.2 mmol). The reaction mixture was warmed to room temperature and stirred for 1 h, heated to 40° C. for 2 h, and additional AcOH (0.035 mL, 0.61 mmol) and TBAF (0.60 mL, 1 M in THF, 0.60 mmol) were added. Stirring was continued at 40° C. After 3 h, the reaction mixture was poured into water (300 mL). The precipitate that formed was collected by filtration, washed with water, and dried under high vacuum. Purification by flash column chromatography on silica gel (eluted with 50% to 100% EtOAc in hexanes gave 4-(4-(1H-1,2,3-triazol-1-yl)phenyl)-5-chlorothiazol-2-amine.

Provenance & Evidence