Reacción #2256

Ecuación de reacción

N-[3-chloro-phenyl]-4-(2-carboxy-4-pyridyl)-2-pyrimidineamine

N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride

N-hydroxysuccinimide

ethylenediamine

→

N-[3-chloro-phenyl]-4-[2-(N-{2-amino-ethyl}-aminocarbonyl)-4-pyridyl]-2-pyrimidineamine hydrochloride

Disolventes

ethyl acetate

dimethylformamide

DMF

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGAfter stirring for 14 h at RT
2. 2
   Extracciónextracted with 30 ml of water
3. 3
   SecadoThe organic phase is dried (sodium sulfate)
4. 4
   Concentraciónconcentrated
5. 5
   OtroCrystallisation from isopropanol/ethanolic hydrochloric acid

Procedimiento

80 mg (0.24 mmol) of N-[3-chloro-phenyl]-4-(2-carboxy-4-pyridyl)-2-pyrimidineamine, 70.8 mg (0.36 mmol) of N-ethyl-N'-(3-dimethylaminopropyl)-carbodiimide hydrochloride and 42 mg (0.36 mmol) of N-hydroxysuccinimide are dissolved in 3 ml of dimethylformamide and stirred for 2.5 h at RT. The reaction mixture is then added dropwise at 0° within a period of 30 minutes to a solution of 0.77 ml (11.8 mmol) of ethylenediamine in 2 ml of DMF. After stirring for 14 h at RT, the reaction mixture is poured into 50 ml of ethyl acetate and extracted with 30 ml of water. The organic phase is dried (sodium sulfate) and concentrated. Crystallisation from isopropanol/ethanolic hydrochloric acid gives N-[3-chloro-phenyl]-4-[2-(N-{2-amino-ethyl}-aminocarbonyl)-4-pyridyl]-2-pyrimidineamine hydrochloride; m.p. 161°-163°, FAB-MS: 369 (M+ +H).

Fuente