5-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide → 5-Hydroxy-1-methyl-6-oxo-2-m-tolylmethanesulfonylamino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamide

HRID 1409592Notes

Reaction equation

HRID 1409592 reaction equation
C([O:8][C:9]1[C:14](=[O:15])[N:13]([CH3:16])[C:12]([NH:17][S:18]([CH2:21][C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)(=[O:20])=[O:19])=[N:11][C:10]=1[C:29]([NH:31][CH3:32])=[O:30])C1C=CC=CC=1>[Pd].C(OCC)(=O)C.CO>[CH3:32][NH:31][C:29]([C:10]1[N:11]=[C:12]([NH:17][S:18]([CH2:21][C:22]2[CH:23]=[C:24]([CH3:28])[CH:25]=[CH:26][CH:27]=2)(=[O:19])=[O:20])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=1[OH:8])=[O:30]

Participants

5

Reactant 1

HCID 867102905-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide

Product 1

HCID 867102915-Hydroxy-1-methyl-6-oxo-2-m-tolylmethanesulfonylamino-1,6-dihydro-pyrimidine-4-carboxylic acid methylamideYield 53.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Palladium on carbon 10% (20 mg, 18.8 μmol) was added to a round-bottomed flask containing a solution of 5-(benzyloxy)-N,1-dimethyl-6-oxo-2-(m-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide (0.07 g, 153 μmol) in ethyl acetate (5 ml) and MeOH (5 ml). The resulting mixture was degassed by nitrogen, evacuated and purged with hydrogen. The mixture was stirred at room temperature under an atmosphere of hydrogen for one hour, filtered and evaporated to dryness under reduced pressure. The residue was washed with hexane and DCM, and crystallized from MeOH/Et2O to give the title compound as an off-white solid (0.03 g; 53%). LCMS m/z=367 (MH+).

Workup

  1. customThe resulting mixture was degassed by nitrogen
  2. customevacuated
  3. custompurged with hydrogen
  4. filtrationfiltered
  5. customevaporated to dryness under reduced pressure
  6. washThe residue was washed with hexane and DCM
  7. customcrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-a3a4f079797344f888184e9e2046b233
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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