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

HRID 875945

Reaction equation

HRID 875945 reaction equation
[Br:1][C:2]1[C:3](Cl)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1.[CH:10]1([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11]1>CN1CCCC1=O.C(OCC)(=O)C>[Br:1][C:2]1[C:3]([N:16]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:4][C:5]([Cl:8])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 74567N-CyclohexylanilineHCID 2899735-Bromo-2,4-dichloropyrimidine

Product 1

HCID 58299589(5-Bromo-2-chloro-pyrimidin-4-yl)-cyclohexyl-phenyl-amineYield 24%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

5-Bromo-2,4-dichloropyrimidine (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).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. washwashed with water and brine
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customPurification by flash chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-a85591db25ab4614b9c75c3381179b3d
Source dataset
uspto-grants-2015_03
Patent number
US08980903B2

Linked notes

Loading…