2-Chloro-6-methylaniline → 4-[2-[(2-chloro-6-methylphenyl)amino]-4-pyridinyl]-N-(2-methoxy-1-methylethyl)-2-pyrimidinamine

HRID 913288Notes

Reaction equation

HRID 913288 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]([CH3:19])[CH2:16][O:17][CH3:18])[N:9]=2)[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:22]=1[NH2:23].C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:20][C:21]1[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[C:22]=1[NH:23][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][N:11]=[C:10]([NH:14][CH:15]([CH3:19])[CH2:16][O:17][CH3:18])[N:9]=2)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 3

HCID 68972-Chloro-6-methylanilineHCID 10796Cesium carbonateHCID 86646775HCID 86646775, compound2×

Product 1

HCID 673891454-[2-[(2-chloro-6-methylphenyl)amino]-4-pyridinyl]-N-(2-methoxy-1-methylethyl)-2-pyrimidinamine

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 4-(2-chloro-4-pyridinyl)-N-(2-methoxy-1-methylethyl)-2-pyrimidinamine (i.e., the product of Step B) (100 mg, 0.35 mmol) in toluene (10 mL) was added 2-chloro-6-methylaniline (102 mg, 0.72 mmol), cesium carbonate (350 mg, 1.07 mmol), palladium(II) acetate (4 mg, 0.017 mmol) and ((±)-BINAP) (22 mg, 0.035 mmol), and the resulting mixture was stirred at reflux for 30 h. After cooling to room temperature, the mixture was concentrated, and purified using column chromatography on silica gel eluted with 40% ethyl acetate in hexanes to give 30 mg of the title compound as a solid.

Workup

  1. temperatureat reflux for 30 h
  2. concentrationthe mixture was concentrated
  3. custompurified
  4. washeluted with 40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6897530edede4bc380f1d54a73e03c54
Source dataset
uspto-grants-2011_09
Patent number
US08026359B2

Reaction notes

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