Water → HCID 67470507, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-(6-(1H-tetrazol-1-yl)pyridin-3-yloxy)-1-(piperidin-4-yl)pyrrolidin-2-one bishydrochloride salt (101 mg, 0.25 mmol) and DIEA (0.30 mL, 1.75 mmol) in DMF (3 mL) was added 2-chloro-5-ethylpyrimidine (71 mg, 0.50 mmol). The reaction was heated at 100° C. for 6 hours. The reaction was cooled to ambient temperature and diluted by the addition of water (5 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The material was purified by silica gel chromatography eluting with a gradient of 2:1 hexanes/EtOAc up to 100% EtOAc to yield 3-(6-(1H-tetrazol-1-yl)pyridin-3-yloxy)-1-(1-(5-ethylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one (52 mg, 48%) as an off white solid. Mass spectrum (apci) m/z=383.2 (M-N3CH+3H).

Provenance & Evidence