5-Bromo-1,3-phenylenediamine

To the solution of 1-bromo-3, 5-dinitrobenzene (10 g, 40 mmol) in methanol: water (V/ V: 50 mL/ 50 mL) was added ammonium chloride (17.33g, 323.9 mmol) and iron powder (11.31 g, 202.5 mmol). The resulting mixture washeated at 95 °C overnight, filtered through celite and concentrated to removemethanol. The aqueous solution was extracted with dichloromethane and thecombined organic layers were washed with water, brine, dried over NaGeneral procedure: Nitroarene 1 (0.1 mmol), anhydrous ethanol (3 ml) and the catalyst (3.9 mg or7.9 mg, see Table 2) were placed in an RHP30ML high pressure reactor(www.openscience.ru) equipped with a magnetic stirrer. The reactor waspurged with argon, purged and filled with hydrogen, then heated to 80 °C and its content was stirred for 20 h. After the reaction completion, the mixture was centrifuged for 10 min and the solution was decanted.The catalyst was washed with ethanol (2×5 ml) in the same manner. Thecombined centrifugate was concentrated in a rotary evaporator, the residuewas dissolved in CDCl3 and analyzed by 1H NMR (400 MHz).To the solution of 1-bromo-3, 5-dinitrobenzene (10 g, 40 mmol) in methanol: water (V/ V: 50 mL/ 50 mL) was added ammonium chloride (17.33g, 323.9 mmol) and iron powder (11.31 g, 202.5 mmol). The resulting mixture washeated at 95 °C overnight, filtered through celite and concentrated to removemethanol. The aqueous solution was extracted with dichloromethane and thecombined organic layers were washed with water, brine, dried over NaGeneral procedure: Nitroarene 1 (0.1 mmol), anhydrous ethanol (3 ml) and the catalyst (3.9 mg or7.9 mg, see Table 2) were placed in an RHP30ML high pressure reactor(www.openscience.ru) equipped with a magnetic stirrer. The reactor waspurged with argon, purged and filled with hydrogen, then heated to 80 °C and its content was stirred for 20 h. After the reaction completion, the mixture was centrifuged for 10 min and the solution was decanted.The catalyst was washed with ethanol (2×5 ml) in the same manner. Thecombined centrifugate was concentrated in a rotary evaporator, the residuewas dissolved in CDCl3 and analyzed by 1H NMR (400 MHz).General procedure: To a mixture of 5-substituted-2, 4-dichloropyrimidines 1a-j (1.00g, 5.52mmol) and benzene-1, 3-diamines 2a-j (0.59g, 5.52mmol) was dissolved in n-butanol (10mL) and DIPEA (1.42g, 11.04mmol) was added and the reaction mixture was stirred at room temperature. The reaction was continued until complete consumption of starting material, monitored by TLC, for 2'8h. The solvent was removed under reduced pressure and the residue was dissolved in EtOAc. Organic layer was washed with water, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash column chromatography (SiO2, Hexanes/EtOAc) to afford the compounds 3a-j.

Molecular Weight:187.04
XLogP3:1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:185.97926
Monoisotopic Mass:185.97926
Topological Polar Surface Area:52
Heavy Atom Count:9
Complexity:87.1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes