Reacción #166296

Ecuación de reacción

Compound 37

(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amine

4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester

→

compound 38

Rendimiento 33.0%

4-{-4-[5-Bromo-4-(cyclohexyl-phenyl-amino)-pyrimidin-2-ylamino]-phenyl}-piperazine-1-carboxylic acid tert-butyl ester

Rendimiento 33.0%

Disolventes

ethyl acetate

dioxane

Condiciones de reacción

Tratamiento posterior

1. 1
   TemperaturaThe reaction was cooled to room temperature
2. 2
   LavadoThis mixture was washed with water and brine
3. 3
   SecadoThe organic layer was dried with sodium sulfate
4. 4
   Otropurified by flash chromatography (ethyl acetate/hexane)

Procedimiento

Compound 37 (0.42 g, 1.15 mmol) and 4-(4-amino-phenyl)-piperazine-1-carboxylic acid tert-butyl ester (0.64 g, 2.30 mmol) were dissolved in dioxane (2 mL), and this mixture was heated at 100° C. for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate. This mixture was washed with water and brine. The organic layer was dried with sodium sulfate and purified by flash chromatography (ethyl acetate/hexane) to give compound 38 as a yellow solid (0.23 g, 33%). 1H NMR (500 MHz, DMSO-d6) δ ppm 9.18 (1 H, s), 7.97 (1 H, s), 7.55 (2 H, d, J=10 Hz), 7.37 (2 H, m), 7.31 (1 H, m), 7.12 (2 H, m), 6.89 (2 H, d, J=10 Hz), 4.68 (1 H, m), 3.44 (4 H, m), 3.00 (4 H, m), 1.91 (2 H, d, J=10 Hz), 1.72 (2 H, d, J=10 Hz), 1.57 (1 H, d, J=10 Hz), 1.41 (9 H, s), 1.35 (2 H, m), 1.14 (2 H, m), 0.92 (1 H, m); LCMS-ESI (POS), M/Z, M+1: Found 609.2, Calculated 607.2/609.2.

Fuente