5-(2-Methyl-5-nitrophenyl)pyrimidine → 4-Methyl-3-(pyrimidin-5-yl)aniline

HRID 1835466Notes

Reaction equation

HRID 1835466 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[C:11]1[CH:12]=[N:13][CH:14]=[N:15][CH:16]=1>O1CCCC1.CO.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([C:11]2[CH:16]=[N:15][CH:14]=[N:13][CH:12]=2)[CH:4]=1

Participants

5

Reactant 1

HCID 235036925-(2-Methyl-5-nitrophenyl)pyrimidine

Product 1

HCID 235036604-Methyl-3-(pyrimidin-5-yl)anilineYield 99.7%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-(2-methyl-5-nitrophenyl)pyrimidine (0.431 g) in tetrahydrofuran (4 ml) and methanol (4 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 129 mg) under hydrogen atmosphere for 2 hours. The catalyst was filtered off, and the filtrate was evaporated under reduced pressure to give 5-(5-amino-2-methylphenyl)pyrimidine (370 mg, 99.7%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-adfc07ada01e42dbaea0a58636652676
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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