Sodium hydride → ((R)-2-{3-(2,6-difluoro-benzyl)-4-methyl-5-[4-(3-nitro-benzyl)-3-oxo-piperazin-1-yl]-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl}-1-phenyl-ethyl)-carbamic acid tert-butyl ester

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Reaction Steps

{(R)-2-[3-(2,6-difluoro-benzyl)-4-methyl-2,6-dioxo-5-(3-oxo-piperazin-1-yl)-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (50 mg, 0.0878 mmol) was dissolved in 1 mL of THF, with nitrogen purge. While on ice, 60% NaH (10 mg, 0.263 mmol) was added to the solution which was then stirred at room temperature for 10 min. Again, while being cooled on ice, 3-nitrobenzyl bromide (23 mg, 0.105 mmol) was added, followed by stirring at room temperature for 1 hr. A little amount of a saturated ammonium chloride solution was added before extraction with dichloromethane. After concentration, the resulting residue was purified by column chromatography eluting with an EtOAc/hexane/dichloromethane (2/1/0.5) eluent to afford 28 mg of the compound (42%).

Provenance & Evidence