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

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.

1. stirringthe reaction mixture was stirred for 2 h
2. stirringthe reaction mixture was stirred for 2 h
3. stirringthe reaction mixture was stirred overnight
4. customThe reaction was quenched with water (20 mL)
5. extractionThe resulting mixture was extracted with EtOAc (10×20 mL)
6. dry with materialthe combined organic extracts were dried over Na2SO4
7. filtrationfiltered
8. customevaporated under reduced pressure
9. customThe crude residue was purified by preparative TLC (DCM/MeOH, 90/10)

ORD record

ord-86bae5a6026c410cbf295f7914be8f62

Source dataset

uspto-grants-2012_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08268840B2