Methanol → HCID 86710294, compound

HRID 1409595Notes

Reaction equation

HRID 1409595 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:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=2)(=[O:20])=[O:19])=[N:11][C:10]=1[C:29]([NH:31][CH3:32])=[O:30])C1C=CC=CC=1.CO>[Pd].C(OCC)(=O)C>[CH3:32][NH:31][C:29]([C:10]1[N:11]=[C:12]([NH:17][S:18]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=2)(=[O:20])=[O:19])[N:13]([CH3:16])[C:14](=[O:15])[C:9]=1[OH:8])=[O:30]

Participants

5

Reactant 2

HCID 887MethanolHCID 86710295HCID 86710295, compound

Product 1

HCID 86710294HCID 86710294, compoundYield 70.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-(benzyloxy)-N, 1-dimethyl-6-oxo-2-(p-tolylmethylsulfonamido)-1,6-dihydro-pyrimidine-4-carboxamide (80 mg, 175 μmol), palladium on carbon (186 mg, 87.6 μmol), MeOH (5 ml) and ethyl acetate (5 ml) was placed under an atmosphere of hydrogen. After stirring for 1.5 hour, the reaction mixture was filtered and evaporated to dryness. Crystallization from MeOH provided the title product as an off-white solid (0.045 g; 70%). LCMS: m/z=367 (MH+).

Workup

  1. filtrationthe reaction mixture was filtered
  2. customevaporated to dryness
  3. customCrystallization from MeOH

Sources & evidence

ORD record
ord-cd511f2cd88d4ef0bd3d012f3d69fc2e
Source dataset
uspto-grants-2014_12
Patent number
US08921388B2

Reaction notes

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