Diisopropylethylamine → [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Participants

Reaction Conditions

Reaction Steps

To a pressure tube was added [(2R)-3-{2-[6-chloro-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.100 g, 0.204 mmol), azetidine hydrochloride (19.1 mg, 0.204 mmol), DIPEA (71.2 μL, 0.408 mmol) and DMSO (2 mL). The tube was sealed and was heated to 65-70° C. with stirring for 3 days. The reaction mixture was then cooled to RT and purified by RP-HPLC to afford [(2R)-3-{2-[6-(1-azetidinyl)-5-fluoro-2-(methylthio)-4-pyrimidinyl]hydrazino}-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (68 mg, 65%). LCMS: (M+H)+: 511.2.

Provenance & Evidence