Tetrabutylammonium Fluoride → HCID 66743388, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-{[tert-butyl(dimethyl)silyl]oxy}-6′-(5-methyl-1H-pyrazol-4-yl)-1′H-spiro[cyclohexane-1,2′-thieno[3,2-d]pyrimidin]-4′(3′H)-one (<0.450 mmol) in THF (4 mL) was added N,N,N,N-tetrabutylammonium fluoride (1.0 M in THF, 1.08 mL, 1.08 mmol). The mixture was stirred at room temperature for 16 h and at 50° C. for 1 h. The mixture was partitioned between EtOAc (20 mL) and aqueous NaHCO3 (10 mL). The aqueous layer was extracted with EtOAc (5 mL×2). The combined organic layers were washed with brine (5 mL), dried over Na2SO4 and concentrated under reduced pressure. The residue was purified by column chromatography (Purif, silica gel, EtOAc to 85:15 EtOAc/MeOH) followed by trituration with EtOAc (5 mL) to give the title compound (32.1 mg, 22%) as a pale yellow solid:

Provenance & Evidence