Dimethyl Sulfoxide → HCID 86730262, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (S)-1-(4-phenoxyphenyl)ethanamine hydrochloride (281 mg, 1.125 mmol), 3-(2-chloro-5-fluoropyrimidin-4-yl)oxazolidin-2-one (103 mg, 0.379 mmol) and DIPEA (0.331 ml, 1.896 mmol) in DMSO was heated to 110° C. for 1 h. LCMS showed little product. Heated for an additional 16 h. LCMS still showed starting material. Added an additional 5 equivalents of DIPEA and 1 equivalent of KF. Heated to 110° C. for 2 h. LCMS shows product. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Purified by column chromatography (10% to 50% EtOAc/Heptane) to give (S)-1-(5-fluoro-2-(1-(4-phenoxyphenyl)ethylamino) pyrimidin-4-yl)-3-oxa-1-azaspiro[4.4]nonan-2-one (62 mg, 0.138 mmol).

Provenance & Evidence