Water → (S)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)pyrrolidin-2-one

Participants

Reaction Conditions

Reaction Steps

To a solution of (S)-3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)-1-(piperidin-4-yl)pyrrolidin-2-one hydrochloride salt (128 mg, 0.198 mmol) and DIEA (0.173 mL, 0.99 mmol) in DMF (3 mL) was added 2-chloro-5-ethylpyrimidine (85 mg, 0.532 mmol). The reaction was heated to 100° C. for 4 hours and then poured into water (10 mL) and EtOAc (10 mL). The organic layer was separated and the aqueous layer extracted with EtOAc (2×5 mL). The combined organic layers were dried with MgSO4 and concentrated in vacuo. The resulting material was purified by silica gel chromatography eluting with a gradient of 1:1 hexanes/EtOAc to EtOAc to yield (S)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)-3-(4-(5-methyl-1H-tetrazol-1-yl)phenoxy)pyrrolidin-2-one (15 mg, 17%) as an off white solid. Mass spectrum (apci) m/z=449.2 (M+H).

Provenance & Evidence