Tetrabutylammonium Fluoride → 5-amino-8-(trans-3-hydroxy-cyclopentyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride (1 M in THF, 0.576 mL) was added dropwise, at RT, under argon atmosphere, to a mixture of 5-amino-8-[trans-3-(tert-butyl-dimethyl-silanyloxy)-cyclopentyl]-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one (200 mg, 0.443 mmol) in anhydrous THF (5 mL) and the resulting mixture was stirred overnight. A second aliquot of solution of tetrabutylammonium fluoride (1 M in THF, 0.6 mL) was then added and the reaction mixture was stirred for 2 h. A third aliquot of solution of tetrabutylammonium fluoride (1 M in THF, 1.8 mL) was then added and the reaction mixture was stirred for 2 h. A fourth aliquot of solution of tetrabutylammonium fluoride (1 M in THF, 1.3 mL) was then added and the reaction mixture was stirred overnight. The reaction was quenched with water (20 mL) followed by NH4Cl (sat'd aq). The resulting mixture was extracted with EtOAc (10×20 mL) and the combined organic extracts were dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by preparative TLC (DCM/MeOH, 90/10) to give 106 mg (82% yield) of 5-amino-8-(trans-3-hydroxy-cyclopentyl)-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one.

Provenance & Evidence