Triethylamine → HCID 178478346, compound

HRID 1801719Notes

Reaction equation

HRID 1801719 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[NH2:9][C:10]1[CH:18]=[CH:17][C:13]2[N:14]=[CH:15][NH:16][C:12]=2[CH:11]=1.CCN(CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:9][C:10]2[CH:18]=[CH:17][C:13]3[NH:14][CH:15]=[N:16][C:12]=3[CH:11]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 136235-AminobenzimidazoleHCID 775312,4-Dichloropyrimidine

Product 1

HCID 178478346HCID 178478346, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (1 mmol) and 5-Aminobenzimidazole (1 mmol) in 5 ml EtOH, was added Et3N (1 mmol). The reaction mixture was refluxed for 5 hours. After removal of the solvent in vacuo and addition of H2O, the mixture was extracted with EtOAc. The organic layers were combined, washed with a saturated NaCl aqueous solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-1H-benzo[d]imidazol-5-amine in a yield of 80%.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 hours
  2. customAfter removal of the solvent
  3. additionin vacuo and addition of H2O
  4. extractionthe mixture was extracted with EtOAc
  5. washwashed with a saturated NaCl aqueous solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-3a833b257b25457daf479a0490e6315b
Source dataset
uspto-grants-2013_01
Patent number
US08349859B2

Reaction notes

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