3-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide → 3-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]-amino]tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide

HRID 2351092Notes

Reaction equation

HRID 2351092 reaction equation
C1(C[O:8][C:9]2[C:14]([O:15]CC3C=CC=CC=3)=[CH:13][N:12]=[C:11]([C:23]([NH:25][N:26]3[CH2:31][CH2:30][CH2:29][N:28]([C:32]([NH2:34])=[O:33])[C:27]3=[O:35])=[O:24])[CH:10]=2)C=CC=CC=1>CN(C)C=O.[Pd]>[OH:15][C:14]1[C:9](=[O:8])[CH:10]=[C:11]([C:23]([NH:25][N:26]2[CH2:31][CH2:30][CH2:29][N:28]([C:32]([NH2:34])=[O:33])[C:27]2=[O:35])=[O:24])[NH:12][CH:13]=1

Participants

4

Reactant 1

HCID 198480113-[[[4,5-Bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide

Product 1

HCID 198480063-[[(1,4-Dihydro-5-hydroxy-4-oxo-2-pyridinyl)carbonyl]-amino]tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

3-[[[4,5-bis(phenylmethoxy)-2-pyridinyl]carbonyl]amino]-tetrahydro-2-oxo-1(2H)-pyrimidinecarboxamide (27.45 g, 57.7 mmol), dissolved in 750 ml N,N-dimethylformamide, was hydrogenated for 1.5 hours over 10 g palladium on activated carbon. The catalyst was removed by filtration and the solvent distilled off in vacuo. The residue was triturated twice with ether to give two batches (15.5 g and 4.0 g) of the desired product, melting point 215°-220° C.

Workup

  1. customThe catalyst was removed by filtration
  2. distillationthe solvent distilled off in vacuo
  3. customThe residue was triturated twice with ether

Sources & evidence

ORD record
ord-e86423f6e8b1443ea5b04aafe4d2961a
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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