N-(5-Nitro-pyrimidin-2-yl)-benzamide → N-(5-aminopyrimidin-2-yl)benzamide

HRID 714577Notes

Reaction equation

HRID 714577 reaction equation
[C:1]([NH:9][C:10]1[N:15]=[CH:14][C:13]([N+:16]([O-])=O)=[CH:12][N:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[Pd].C(O)C>[C:1]([NH:9][C:10]1[N:11]=[CH:12][C:13]([NH2:16])=[CH:14][N:15]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 57699955N-(5-Nitro-pyrimidin-2-yl)-benzamide

Product 1

HCID 11499482N-(5-aminopyrimidin-2-yl)benzamideYield 28.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

2-(N-benzoyl)amino-5-nitropyrimidine (790 mg) was added into ethanol (100 ml). 80 mg of 10% palladium on carbon was added to the solution under stirring at the room temperature. The reactant was hydrogenated and stirred for 4 hr. The solution was filtered through silica gel-sand panel funnel. The filtrate was retained and the solvent was evaporated in vacuo. The resultant substance was purified by flash chromatography with silica gel column and eluated with chloroform:methanol=95:5 to give 2-(N-benzoyl)amino-5-aminopyrimidine (200 mg).

Workup

  1. stirringstirred for 4 hr
  2. filtrationThe solution was filtered through silica gel-sand panel funnel
  3. customthe solvent was evaporated in vacuo
  4. customThe resultant substance was purified by flash chromatography with silica gel column

Sources & evidence

ORD record
ord-a03a4350830240c39d6059b591a9b038
Source dataset
uspto-grants-2015_11
Patent number
US09187458B2

Reaction notes

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