1,2-Dichloroethane → [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide

Participants

Reaction Steps

To a solution of (3S)-1-(2-chloro-5-fluoro-6-hydrazino-4-pyrimidinyl)-4,4-dimethyl-3-pyrrolidinol (0.131 g, 0.475 mmol) in DMF (3 mL) was added added (2R)-3-cyclopentyl-2-{[formyl(tetrahydro-2H-pyran-2-yloxy)amino]methyl}propanoic acid (0.1181 g, 0.395 mmol), N-methylmorpholine (0.220 ml, 2.001 mmol), 1-hydroxy-7-azabenzotriazole (64 mg, 0.470 mmol), and EDC (91 mg, 0.475 mmol). The solution was stirred overnight and then purified directly by Gilson RPLC to afford [(2R)-3-(2-{2-chloro-5-fluoro-6-[(4S)-4-hydroxy-3,3-dimethyl-1-pyrrolidinyl]-4-pyrimidinyl}hydrazino)-2-(cyclopentylmethyl)-3-oxopropyl](tetrahydro-2H-pyran-2-yloxy)formamide (0.1294 g, 59% yield) as an orange oil. LCMS: (M+H)+: 557.3.

Provenance & Evidence