{(R)-2-[3-(2,6-difluoro-benzyl)-5-nitro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester → HCID 67143363, compound

HRID 574249Notes

Reaction equation

HRID 574249 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([N+:17]([O-])=O)=[CH:13][N:12]([CH2:20][C:21]2[C:26]([F:27])=[CH:25][CH:24]=[CH:23][C:22]=2[F:28])[C:11]1=[O:29])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:36])[NH:7][C@H:8]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:9][N:10]1[C:15](=[O:16])[C:14]([NH2:17])=[CH:13][N:12]([CH2:20][C:21]2[C:22]([F:28])=[CH:23][CH:24]=[CH:25][C:26]=2[F:27])[C:11]1=[O:29])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 87285738{(R)-2-[3-(2,6-difluoro-benzyl)-5-nitro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl esterHCID 178418361HCID 178418361, compound

Product 1

HCID 67143363HCID 67143363, compoundYield 67.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of {(R)-2-[3-(2,6-difluoro-benzyl)-5-nitro-2,6-dioxo-3,6-dihydro-2H-pyrimidin-1-yl]-1-phenyl-ethyl}-carbamic acid tert-butyl ester (173 mg, 0.34 mmol) in methanol (5 mL) was added 10% palladium/carbon (36 mg) in a nitrogen atmosphere, followed by stirring at room temperature for 1 hr in a hydrogen atmosphere. After removal of the palladium/carbon by filtration through celite, the filtrate was concentrated. The residue was purified using silica gel chromatography (eluent: hexane/ethyl acetate/dichloromethane, 1/1/1) and dried in a vacuum to afford 109 mg of the compound as a colorless oil (yield 66%).

Workup

  1. customAfter removal of the palladium/carbon
  2. filtrationby filtration through celite
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified
  5. customdried in a vacuum

Sources & evidence

ORD record
ord-0bdcbb98934343b9b94fb27fdd7d4a88
Source dataset
uspto-grants-2015_05
Patent number
US09034850B2

Reaction notes

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