HCID 19787897, compound → HCID 19787914, compound

HRID 1656507Notes

Reaction equation

HRID 1656507 reaction equation
C(OC([NH:11][C:12]1[C:17](=[O:18])[N:16]([CH2:19][C:20]([NH:22][CH:23]([CH:37]([CH3:39])[CH3:38])[CH:24]([O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=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:37]([CH3:39])[CH3:38])[CH:24]([O:29][Si:30]([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:31])[CH3:32])[C:25]([F:28])([F:27])[F:26])=[O:21])[C:15]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)=[N:14][CH:13]=1

Participants

5

Reactant 1

HCID 19787897HCID 19787897, compound

Product 1

HCID 19787914HCID 19787914, compoundYield 88.5%

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-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (12.4 g) in tetrahydrofuran (100 mL) and ethanol (60 mL) was added 10% (w/w) palladium on carbon (1 g) and the suspension was placed under a hydrogen atmosphere (3.4 bar) and shaken for 12 h. The solution was filtered through diatomaceous earth to give an oil which crystallized from ether to provide 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a white solid (8.7 g); MS: m/z=513(M+1).

Workup

  1. filtrationThe solution was filtered through diatomaceous earth
  2. customto give an oil which
  3. customcrystallized from ether

Sources & evidence

ORD record
ord-d901f490fe994a828b1de93222f1ace3
Source dataset
uspto-grants-1993_10
Patent number
US05254558

Reaction notes

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