Water → HCID 22236145, compound

Participants

Reaction Conditions

Reaction Steps

To 2-[(5-bromo-2-pyrimidinyl)amino]-N-(cyanomethyl)-4-methylpentanamide (123 mg, 0.377 mmol) and 4-[4-(tert-butoxycarbonyl)-1-piperazinyl]phenylboronic acid (140 mg, 0.453 mmol) in DMF (10 mL) under dry nitrogen was added aqueous sodium carbonate (2 M, 0.6 mL, 1.2 mmol) followed by the catalyst PdCl2(dppf) (15 mg, 0.0113 mmol). The reaction was heated to 90° C. for 0.5 hours and more PdCl2(dppf) (15 mg, 0.0113 mmol) was added and the reaction mixture was heated for another 5.5 hours. Water was added and the product extracted with ether (2×), dried over Na2SO4, concentrated in vacuo, and purified by flash chromatography over silica gel (EtOAc/Hex, 7/3) to afford tert-butyl 4-(4-{2-[(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutyl)amino]-5-pyrimidinyl}phenyl)-1-piperazinecarboxylate.

Provenance & Evidence