Triethylamine → 6-(2-chloropyrimidin-4-ylamino)-N,2-dimethylbenzofuran-3-carboxamide

HRID 16236Notes

Reaction equation

HRID 16236 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:30]=[CH:29][C:20]2[C:21]([C:25]([NH:27][CH3:28])=[O:26])=[C:22]([CH3:24])[O:23][C:19]=2[CH:18]=1>CCO>[Cl:8][C:9]1[N:14]=[C:13]([NH:16][C:17]2[CH:30]=[CH:29][C:20]3[C:21]([C:25]([NH:27][CH3:28])=[O:26])=[C:22]([CH3:24])[O:23][C:19]=3[CH:18]=2)[CH:12]=[CH:11][N:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 597308036-amino-N,2-dimethylbenzofuran-3-carboxamide

Product 1

HCID 592247466-(2-chloropyrimidin-4-ylamino)-N,2-dimethylbenzofuran-3-carboxamideYield 80%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Et3N (1 mmol) was added to a solution of 2,4-dichloropyrimidine (1 mmol) and 6-amino-N,2-dimethylbenzofuran-3-carboxamide (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 subjected to extraction with EtOAc. The organic layers were combined, washed with water and brine sequentially, dried over anhydrous Na2SO4, and concentrated in vacuo. The resulting residue was purified by column chromatography to give 6-(2-chloropyrimidin-4-ylamino)-N,2-dimethylbenzofuran-3-carboxamide 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 subjected to extraction with EtOAc
  5. washwashed with water and brine sequentially
  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-8c822fe44f9b48d29be898fc7bcb9c37
Source dataset
uspto-grants-2010_06
Patent number
US07737157B2

Reaction notes

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