Tetrabutylammonium Fluoride → Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-(1-methyltriazol-4-yl)-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate

Participants

Reaction Steps

Ethyl 1-[5-[2-(ethylcarbamoylamino)-7-[1-(trimethylsilylmethyl)triazol-4-yl]-1,3-benzothiazol-5-yl]pyrimidin-2-yl]-4-methyl-piperidine-4-carboxylate (95 mg, 0.1529 mmol) in 1 mL of THF was cooled to 0° C. Water (5 drops) was added followed by tetra butyl ammonium fluoride (0.153 mL, 1.0 M solution in THF). The reaction was stirred at rt for 18 hours, another 0.2 mL of tetra butyl ammonium fluoride solution added and stirred for another 24 hours. The reaction was filtered through a pad of keiselguhr and the solvent removed under vacuum to yield a brown gum. The crude material was purified by preperative HPLC to give the product as a brown gum 63 mg, 75% yield.

Provenance & Evidence