M-Phenylenediamine → HCID 57708355, compound

HRID 929822Notes

Reaction equation

HRID 929822 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[CH:10]=2)[CH:3]=1.[C:16]1([NH2:23])[CH:21]=[CH:20][CH:19]=[C:18]([NH2:22])[CH:17]=1>CCCCO>[Br:15][C:11]1[CH:10]=[C:9]([NH:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:22][C:18]3[CH:17]=[C:16]([NH2:23])[CH:21]=[CH:20][CH:19]=3)[CH:3]=2)[CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 61279992HCID 61279992, compound

Product 1

HCID 57708355HCID 57708355, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of (6-chloro-pyrimidin-4-yl)-(3-bromo-phenyl)-amine (300 mg, 1.1 mmol) and benzene-1,3-diamine (300 mg, 2.75 mmol) in 3 mL of n-BuOH was heated in a scaled tube to 150° C. for 16 hr. Solvent was removed by vacuum evaporation and the crude product was purified by flash chromatography on silica gel with EtOAc/DCM solvent system to afford 255 mg (65% yield) of the title compound as a yellow solid. MS (m/z): MH+=356, 358.

Workup

  1. customSolvent was removed by vacuum evaporation
  2. customthe crude product was purified by flash chromatography on silica gel with EtOAc/DCM solvent system

Sources & evidence

ORD record
ord-ddfc1fd747c74746a649613e015bdd96
Source dataset
uspto-grants-2016_03
Patent number
US09296704B2

Reaction notes

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