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

HRID 1767722Notes

Reaction equation

HRID 1767722 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>[Pt].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 14.2%

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 702EthanolSolvent

Procedure

10% Platinum on carbon (71 mg, 0.036 mmol) was added to a solution 2-(N-benzoyl)amino-5-nitropyrimidine (733 mg, 3.00 mmol) in ethanol (100 ml) at ambient temperature and the reaction stirred for 1 hour under an atmosphere of hydrogen. The reaction was filtered through a pad of celite and the solvents were evaporated in vacuo. Purification by flash chromatography on silica gel, eluting with 5% methanol in dichloromethane yielded 2-(N-benzoyl)amino-5-aminopyrimidine (91 mg, 14% yield) as white solid:

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. customthe solvents were evaporated in vacuo
  3. customPurification by flash chromatography on silica gel
  4. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-6c3114e433d3424f97430d256d64ca11
Source dataset
uspto-grants-2007_06
Patent number
US07235559B1

Reaction notes

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