4-(3,4-Dinitro-phenoxy)-2-methylsulfanyl-pyrimidine → 4-(2-Methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine

HRID 491640Notes

Reaction equation

HRID 491640 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][C:18]=1[N+:19]([O-])=O)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14][CH3:15])[N:9]=1)([O-])=O>CO.[Pd]>[CH3:15][S:14][C:10]1[N:9]=[C:8]([O:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:18]([NH2:19])=[CH:17][CH:16]=2)[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 1

HCID 177564914-(3,4-Dinitro-phenoxy)-2-methylsulfanyl-pyrimidine

Product 1

HCID 177564954-(2-Methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

4-(3,4-Dinitro-phenoxy)-2-methylsulfanyl-pyrimidine (Step A, 1.0 g, 3.2 mmol, 1.0 eq.) was dissolved in MeOH (10 mL) and the atmosphere was replaced by argon. A catalytic amount of 10% Pd/C was added and the argon was replaced by a H2 atmosphere. The mixture was hydrogenated for 2 h at RT at 60 psi using a Parr hydrogenation apparatus. More Pd/C was added and the mixture was hydrogenated for another 4 h at 60 psi. The Pd/C was removed by filtration. The crude aniline was purified using column chromatography (0-100% EtOAc in hexanes) to give 4-(2-methylsulfanyl-pyrimidin-4-yloxy)-benzene-1,2-diamine.

Workup

  1. waitthe mixture was hydrogenated for another 4 h at 60 psi
  2. customThe Pd/C was removed by filtration
  3. customThe crude aniline was purified

Sources & evidence

ORD record
ord-28885475c9d54c58b6733f74830c0321
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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