Reacción #56891

Ecuación de reacción

sodium chloride

hydrochloric acid

4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-butyric acid ethyl ester

sodium hydroxide

→

title compound

Rendimiento 66.0%

4-{4-[2-Amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin4-ylamino]-phenyl}-butyric acid

Rendimiento 66.0%

Disolventes

Ethyl acetate

ethanol

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGthe mixture was stirred for 10 minutes
2. 2
   ConcentraciónThe organic layer was concentrated under reduced pressure
3. 3
   workup.ADDITIONThe residual solid was treated with water (25 ml)
4. 4
   workup.STIRRINGstirred vigorously
5. 5
   FiltraciónSuction filtration

Procedimiento

A mixture of 4-{4-[2-amino-6-(5-chloro-2-ethoxy-phenyl)-pyrimidin-4-ylamino]-phenyl}-butyric acid ethyl ester (350 mg, 0.71 mmol), sodium hydroxide (150 mg, 3.8 mmol) and ethanol (5 ml) was stirred for 18 hours. Ethyl acetate (100 ml), saturated aqueous sodium chloride solution (100 ml) and concentrated hydrochloric acid (1 ml) were added and the mixture was stirred for 10 minutes. The organic layer was concentrated under reduced pressure. The residual solid was treated with water (25 ml) and stirred vigorously. Suction filtration afforded the title compound (200 mg 61% yield) as a white powder. 1H NMR (DMSO-d6) δ 1.38 (m, 3H, CH3), 1.83 (m, 2H, CH2), 2.23 (m, 2H, CH2), 2.61 (m, 2H, CH2), 4.17 (m, 2H, CH2), 6.60 (s, 1H, Ar), 7.20-7.29 (m, 3H, Ar), 7.61-7.71 (m, 4H, Ar), 10.76 (s, 1H, NH), 12.48 (s, 1H).

Fuente