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

HRID 491645Notes

Reaction equation

HRID 491645 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:18]=[CH:19][C:20]=1[N+:21]([O-])=O)[O:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([S:14]([CH3:17])(=[O:16])=[O:15])[N:9]=1)([O-])=O>CO.[Pd]>[CH3:17][S:14]([C:10]1[N:9]=[C:8]([O:7][C:6]2[CH:5]=[C:4]([NH2:1])[C:20]([NH2:21])=[CH:19][CH:18]=2)[CH:13]=[CH:12][N:11]=1)(=[O:15])=[O:16]

Participants

4

Reactant 1

HCID 177560784-(3,4-Dinitro-phenoxy)-2-methylsulfonyl-pyrimidine

Product 1

HCID 177564964-(2-Methanesulfonyl-pyrimidin-4-yloxy)-benzene-1,2-diamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 887MethanolSolvent

Procedure

4-(3,4-Dinitro-phenoxy)-2-methylsulfonyl-pyrimidine (Step A, 1.0 g, 2.9 mmol, 1.0 eq.) was dissolved in MeOH (50 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 stirred for 16 h at RT at atmospheric pressure. More Pd/C was added after the atm was replaced by argon, then the reaction was stirred under H2 at RT for 48 h. The Pd/C was filtered off and the crude aniline was purified using column chromatography (0-100% EtOAc in hexanes) to give 4-(2-methanesulfonyl-pyrimidin-4-yloxy)-benzene-1,2-diamine.

Workup

  1. stirringthe reaction was stirred under H2 at RT for 48 h
  2. filtrationThe Pd/C was filtered off
  3. customthe crude aniline was purified

Sources & evidence

ORD record
ord-308c371357b947cf95d803e086af98f8
Source dataset
uspto-grants-2009_05
Patent number
US07531553B2

Reaction notes

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