Reaction #166295

Reaction equation

5-Bromo-2,4-dichloro-pyrimidine

cyclohexyl-phenyl-amine

→

compound 37

Yield 24.0%

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

Yield 24.0%

Solvents

ethyl acetate

N-methylpyrrolidone

Conditions

Workup

1. 1
   TemperatureThe reaction was cooled to room temperature
2. 2
   Washwashed with water and brine
3. 3
   OtherThe organic phase was dried
4. 4
   Concentrationconcentrated
5. 5
   OtherPurification by flash chromatography (ethyl acetate/hexane)

Procedure

5-Bromo-2,4-dichloro-pyrimidine (2.17 ml, 17.14 mmol) and cyclohexyl-phenyl-amine (2.0 g, 11.43 mmol) were dissolved in N-methylpyrrolidone (NMP) (25 ml), and this reaction was heated to 120° C. for 24 hours. The reaction was cooled to room temperature and diluted with ethyl acetate, washed with water and brine. The organic phase was dried using sodium sulfate and concentrated. Purification by flash chromatography (ethyl acetate/hexane) gave compound 37 as a yellow solid (855 mg, 24%). 1H NMR (500 MHz, DMSO-d6) δ ppm 8.27 (1 H, s), 7.41 (3 H, m), 7.21 (2 H, m), 4.62 (1 H, m), 1.93 (2 H, d, J=10 Hz), 1.75 (2 H, d, J=10 Hz), 1.58 (1 H, d, J=10 Hz), 1.34 (2 H, m), 1.15 (2 H, m), 0.91 (1 H, m).

Source