HCID 12130786, compound → 3-(Pyrimidin-4-yl)aniline

HRID 581918Notes

Reaction equation

HRID 581918 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]2[CH:15]=[CH:14][N:13]=[CH:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 1

HCID 12130786HCID 12130786, compound

Product 1

HCID 124561713-(Pyrimidin-4-yl)anilineYield 96.1%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of (57) (6.3 g, 31 mmol) in a mixture of MeOH (60 ml) and THF (30 ml) was added 5% palladium on activated carbon (300 mg) and the mixture was hydrogenated at ambient pressure for 1 hr. The mixture was filtered and concentrated under reduced pressure. The residue was purified by column-chromatography on silica gel using a mixture of hexane and ethylacetate (3:1) as the eluent to give (58) (5.1 g, 96%).

Workup

  1. filtrationThe mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by column-chromatography on silica gel using
  4. additiona mixture of hexane and ethylacetate (3:1) as the eluent

Sources & evidence

ORD record
ord-a5069e84f2b04ef59b17fbd933c68f11
Source dataset
uspto-grants-1999_07
Patent number
US05922725

Reaction notes

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