Reacción #56813

Ecuación de reacción

title compound

6-(5-Chloro-2-methoxy-phenyl)-N*4*-(4-nitro-phenyl)-pyrimidine-2,4-diamine

tin (II) chloride

hydrochloric acid

→

title compound

Rendimiento 64.0%

N*4*-(4-Amino-phenyl)-6-(5-chloro-2-methoxy-phenyl)-pyrimidine-2,4-diamine

Rendimiento 64.0%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas heated
2. 2
   Temperaturaunder reflux for 2 hours
3. 3
   OtroAfter evaporation of volatiles under reduced pressure
4. 4
   workup.ADDITIONthe residue was treated with aqueous sodium hydroxide solution (1.0 M, 10 ml)
5. 5
   FiltraciónFiltration

Procedimiento

A mixture of the title compound of Example 11 (0.060 g, 0.16 mmol) and tin (II) chloride (0.19 g, 1.0 mmol) in a solution of 1.0 M hydrochloric acid and methanol (1:10, 15 ml) was heated under reflux for 2 hours. After evaporation of volatiles under reduced pressure, the residue was treated with aqueous sodium hydroxide solution (1.0 M, 10 ml) and stirred for 15 minutes. Filtration provided the title compound (0.035 g, 64% yield) as a white powder. 1H NMR (DMSO-d6) δ 3.84 (s, 3H, CH3), 4.83 (s, 2H, NH2), 6.08 (s, 2H, NH2), 6.54 (d, 2H, J=8.7 Hz, Ar), 6.58 (s, 1H, Ar), 7.13 (d, 1H, J=8.9 Hz, Ar), 7.25 (d, 2H, J=8.7 Hz, Ar), 7.41 (dd, 1H, J=8.9 Hz, J-2.8 Hz, Ar), 7.89 (d, 1H, J=2.8 Hz, Ar), 8.67 (s, 1H, NH).

Fuente