Triethylamine → N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amine

HRID 1801713Notes

Reaction equation

HRID 1801713 reaction equation
CCN(CC)CC.[Cl:8][C:9]1[N:14]=[C:13](Cl)[CH:12]=[CH:11][N:10]=1.[NH2:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([CH3:26])=[CH:20]2>CCO>[Cl:8][C:9]1[N:14]=[C:13]([NH:16][C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[NH:22][C:21]([CH3:26])=[CH:20]3)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 27339925-Amino-2-methylindole

Product 1

HCID 59823198N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-5-amineYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Et3N (1 mmol) was added to a solution of 2,4-dichloropyrimidine (1 mmol) and 5-amino-2-methylindole (1 mmol) in 5 ml EtOH. 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 saturated NaCl solution, dried over anhydrous Na2SO4, and concentrated in vacuo. The resulting residue was purified by column chromatography to give N-(2-chloropyrimidin-4-yl)-2-methyl-1H-indol-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 saturated NaCl solution
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe resulting residue was purified by column chromatography

Sources & evidence

ORD record
ord-d2a09a47960f446397296d2a87439c64
Source dataset
uspto-grants-2013_01
Patent number
US08349859B2

Reaction notes

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