N,N'-Dicyclohexylurea → 1,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

HRID 2351085Notes

Reaction equation

HRID 2351085 reaction equation
[O:1]=[C:2]1[C:7]([O:8]CC2C=CC=CC=2)=[CH:6][NH:5][C:4]([C:16]([NH:18][N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])=[O:17])=[CH:3]1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.C(NC1CCCCC1)(NC1CCCCC1)=O>C(#N)C>[OH:8][C:7]1[C:2](=[O:1])[CH:3]=[C:4]([C:16]([NH:18][N:19]2[CH2:24][CH2:23][CH2:22][NH:21][C:20]2=[O:25])=[O:17])[NH:5][CH:6]=1

Participants

5

Reactant 3

HCID 4277N,N'-DicyclohexylureaHCID 11708267BistrimethylsilylacetamidHCID 198480031,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide

Product 1

HCID 198480131,4-Dihydro-5-hydroxy-4-oxo-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridinecarboxamide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.71 g. (ca. 5 mmol) crude 1,4-dihydro-4-oxo-5-(phenylmethoxy)-N-(tetrahydro-2-oxo-1(2H)-pyrimidinyl)-2-pyridine-carboxamide in 22 ml acetonitrile was added 4.1 g (20 mmol) bis(trimethylsilyl)acetamide. After stirring for 20 minutes the undissolved dicyclohexylurea was filtered off and 0.85 g palladium on carbon were added to the filtrate. After the mixture had been hydrogenated for one hour, the catalyst was removed by filtration and 2.1 ml methanol and 0.1 ml acetic acid were added to the filtrate. After stirring overnight the desired product was filtered off and dried in vacuo. Yield 0.7 g, melting point 285°-290° C. (dec.).

Workup

  1. additionTo a suspension of 1.71 g
  2. filtrationwas filtered off
  3. addition0.85 g palladium on carbon were added to the filtrate
  4. customthe catalyst was removed by filtration and 2.1 ml methanol and 0.1 ml acetic acid
  5. additionwere added to the filtrate
  6. filtrationwas filtered off
  7. customdried in vacuo

Sources & evidence

ORD record
ord-7f931630bbd84374a778080aa84c9a6e
Source dataset
uspto-grants-1989_10
Patent number
US04871841

Reaction notes

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