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

HRID 1835455Notes

Reaction equation

HRID 1835455 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[N:10][CH:11]=[N:12][CH:13]=2)=[CH:4][C:3]=1[N+:14]([O-])=O>O1CCCC1.CO.[Pd]>[NH2:14][C:3]1[CH:4]=[C:5]([C:8]2[CH:13]=[N:12][CH:11]=[N:10][CH:9]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 235036635-(4-Methyl-3-nitrophenyl)-pyrimidine

Product 1

HCID 235036782-Methyl-5-(pyrimidin-5-YL)anilineYield 184.6%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A suspension of 5-(4-methyl-3-nitrophenyl)-pyrimidine (258 mg) in tetrahydrofuran (5ml) and methanol (5 ml) was hydrogenated over palladium on carbon (10% w/w, 50% wet, 130 mg) under hydrogen atmosphere for 4 hours. The catalyst was filtered off and the filtrate was evaporated to give 5-(3-amino4-methylphenyl)pyrimidine(410 mg, 96.5%).

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-2aaf6e3cc2b34a47b1400f7669979dda
Source dataset
uspto-grants-2004_08
Patent number
US06770667B1

Reaction notes

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