Tetrabutylammonium Fluoride → 2-(5-hydroxymethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide

Participants

Reaction Steps

To a solution of 2-[5-(tert-butyl-dimethyl-silanyloxymethyl)-1-methyl-1H-indazol-3-yl]-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (106 mg, 0.17 mmol) in THF (2 mL) was added tetrabutylammonium fluoride (1.0 M in THF, 1.7 mL, 1.7 mmol). The reaction mixture was stirred at room temperature for 10 min then heated at reflux for 2 h. After cooling to room temperature, the reaction was quenched with water and extracted with EtOAc and then with 5% MeOH/CH2Cl2. The combined organic layers were dried over MgSO4 and concentrated. The residue was triturated with EtOAc/MeOH and the solids collected via filtration to afford 30 mg (47%) of 2-(5-hydroxymethyl-1-methyl-1H-indazol-3-yl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide as a light yellow solid.

Provenance & Evidence