HCID 10098504, compound → HCID 19787906, compound

HRID 1656515Notes

Reaction equation

HRID 1656515 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)=[N:14][CH:13]=1)=O)C1C=CC=CC=1>O1CCCC1.C(O)C.[Pd]>[NH2:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:30]([CH3:32])[CH3:31])[C:24](=[O:29])[C:25]([F:27])([F:26])[F:28])=[O:21])[C:15]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)=[N:14][CH:13]=1

Participants

5

Reactant 1

HCID 10098504HCID 10098504, compound

Product 1

HCID 19787906HCID 19787906, compoundYield 80.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(5-benzyloxycarbonylamino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (1.9 g) in tetrahydrofuran (50 mL) and ethanol (50 mL) was added 10% (w/w) palladium on carbon (0.29 g) and the resulting solution was placed under a hydrogen atmosphere (0.75 bar) for 12 h. The catalyst was removed by filtration through diatomaceous earth and the solvent was evaporated. The resulting oil was crystallized from ether. The product was collected and washed with ether:hexane (1:1) to provide 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (1.14 g) as a white solid; NMR (DMSO/D2O): 7.38 (m,6), 4.55 (d,1), 4.37 (d,1), 3.98 (m,1), 2.17 (m,1), 0.79 (d,3), 0.72 (d,3).

Workup

  1. customfor 12 h
  2. customThe catalyst was removed by filtration through diatomaceous earth
  3. customthe solvent was evaporated
  4. customThe resulting oil was crystallized from ether
  5. customThe product was collected
  6. washwashed with ether:hexane (1:1)

Sources & evidence

ORD record
ord-d7acffa6c1064d89837541f864735569
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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