Tetrabutylammonium Fluoride → (S)-(2,4-Dichlorobenzyl)-[1-(5-ethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amine

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Reaction Steps

Add tetrabutylammonium fluoride (1.0 mL, 1.0 mmol, 1.0 M solution in tetrahydrofuran) to a stirred solution of (S)-(2,4-dichlorobenzyl)-[1-(5-trimethylsilanylethynylpyrimidin-2-yl)-pyrrolidin-3-yl]-amine (327 mg, 0.78 mmol) in tetrahydrofuran (10 mL) at 0° C. Warm to room temperature and stir for 1 hour and concentrate to give a residue. Dilute the residue with water (10 mL), extract with ethyl acetate (3×25 mL). Extract the combined organic layers with saturated aqueous sodium chloride (10 mL), concentrate to give a residue. Dissolve the residue in dichloromethane, filter, concentrate to give a residue, and chromatograph the residue on silica gel followed by chromatography on SCX-2 to give the title compound as a yellow gum (194 mg, 72%).

Provenance & Evidence