Triethylamine → HCID 59823277, compound

HRID 1801720Notes

Reaction equation

HRID 1801720 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]1[O:11][C:12]2[CH:18]=[CH:17][C:16](N)=[CH:15][C:13]=2[N:14]=1.CC[N:22](CC)CC>CCO>[Cl:1][C:2]1[N:7]=[C:6]([NH:22][C:17]2[CH:16]=[CH:15][C:13]3[N:14]=[C:10]([CH3:9])[O:11][C:12]=3[CH:18]=2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 775312,4-DichloropyrimidineHCID 7379202-Methyl-1,3-benzoxazol-5-amine

Product 1

HCID 59823277HCID 59823277, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (1 mmol) and 2-methyl-1,3-benzoxazol-5-amine (1 mmol) in 5 ml EtOH was added Et3N (1 mmol). The reaction mixture was refluxed for 5 h. 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-chloro pyrimidin-4-yl)-2-methylbenzo[d]oxazol-6-amine in a yield of 73%.

Workup

  1. temperatureThe reaction mixture was refluxed for 5 h
  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-b90d7aafbb10450b8c8f348924ff6c15
Source dataset
uspto-grants-2013_01
Patent number
US08349859B2

Reaction notes

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