Sodium Hydroxide → 3-{4-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzoimidazol-2-yl]-3-[1,2,4]triazol-1-yl-phenoxy}-2,2-dimethyl-propionic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-{4-[5-(2-Amino-pyrimidin-5-yl)-1-tert-butyl-1H-benzoimidazol-2-yl]-3-[1,2,4]triazol-1-yl-phenoxy}-2,2-dimethyl-propionic acid ethyl ester (example 66) (95 mg, 0.17 mmol) in 1,4-dioxane (10 mL) and H2O (2 mL) is added 3 M NaOH solution (0.17 mL, 0.52 mmol) at room temperature. The solution is stirred at 65° C. for 6 days. The solution is concentrated and the residue is re-dissolved in H2O (5 mL). The pH of the solution is adjusted to 5 with 12N HCl solution. The milky solution is extracted with EtOAc (3×10 mL). The combined organic layer is dried with MgSO4 (500 mg) and is filtered. The filtrate is concentrated and the residue is purified by silica gel flash column chromatography with 10% MeOH in CH2Cl2 as the eluent to afford the title compound (63 mg, 70%). LCMS (ESMS): m/z: 527.40 (M++1).

Provenance & Evidence