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

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Reaction Steps

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.

Provenance & Evidence