Phenol → [2,6-Dimethyl-4-(5-phenoxy-oxazolo[5,4-d]pyrimidin-2-yl)-phenoxy]-acetic acid tert-butyl ester

Participants

Reaction Steps

19 mg of sodium hydride were added under an argon atmosphere to a solution of 38 mg of phenol in 5 ml of dimethylacetamide. After stirring for 30 min at room temperature, a solution of 156 mg of [4-(5-chloro-oxazolo[5,4-d]pyrimidin-2-yl)-2,6-dimethyl-phenoxy]-acetic acid tert-butyl ester in 3 ml of dimethylacetamide was added slowly. The mixture was allowed to stir for 1.5 h at room temperature. Upon consumption of the starting ester an aqueous solution of citric acid (100 g/l) was added until the pH was neutral. The aqueous layer was extracted twice with 15 ml ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and the solvents were removed in vacuo. The title compound was isolated by silica gel chromatography (heptane/ethyl acetate gradient). Yield: 77 mg of a white solid.

Provenance & Evidence