Tetrabutylammonium Fluoride → 8-(4-Fluorophenyl)-1-(3-hydroxypropyl)-N,N,2-trimethyl-1,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide

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Reaction Steps

To the solution of 1-(3-{[tert-butyl(dimethyl)silyl]oxy}propyl)-8-(4-fluorophenyl)-N,N,2-trimethyl-1,6,7,8-tetrahydrochromeno[7,8-d]imidazole-5-carboxamide (35 mg, 0.067 mmol, Step 9) in tetrahydrofuran was added 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.1 mL). The mixture was stirred at room temperature for 2.5 hours. The reaction was quenched by saturated ammonium chloride aqueous solution. The mixture was extracted with ethyl acetate. The combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated in vacuo. The residue was purified by preparative TLC eluting with dichloromethane/methanol (20:1). The obtained product was triturated in hexane to afford the title compound as a pale yellow solid (8.6 mg, 31%)

Provenance & Evidence