2-Chloro-4-(3-nitrophenyl)pyrimidine → 3-(2-Chloropyrimidin-4-yl)aniline

HRID 2386331Notes

Reaction equation

HRID 2386331 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[CH:5]=[CH:4][N:3]=1>C(O)C.[Pt]>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 1

HCID 249018872-Chloro-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 593410233-(2-Chloropyrimidin-4-yl)anilineYield 90%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23939PlatinumSolvent

Procedure

Intermediate 5 was dissolved in ethanol along with 5 mol % of 5% Pt/C. The mixture was stirred under an atmosphere of H2 for 24 hours and then filtered through a pad of Celite to remove catalyst. Removal of the solvent gave product in 90% yield. LC-MS showed purity >95% and the expected M+H+ of 206.

Workup

  1. filtrationfiltered through a pad of Celite
  2. customto remove catalyst
  3. customRemoval of the solvent
  4. customgave product in 90% yield

Sources & evidence

ORD record
ord-07ae0edb07dc409fa1c83319927e6db4
Source dataset
uspto-grants-2012_09
Patent number
US08268822B2

Reaction notes

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