1-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-one → 7-(3-Pyridinyl)[1,2,4]triazolo[1,5-a]pyrimidine

HRID 326089

Reaction equation

HRID 326089 reaction equation
[NH2:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.CN(C)[CH:9]=[CH:10][C:11]([C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=O>C(O)(=O)C>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:11]2[N:3]3[N:4]=[CH:5][N:6]=[C:2]3[N:1]=[CH:9][CH:10]=2)[CH:14]=1

Participants

4

Reactant 2

HCID 5670331-(3-Pyridyl)-3-(dimethylamino)-2-propen-1-oneHCID 178418311HCID 178418311, compound

Product 1

HCID 9009447-(3-Pyridinyl)[1,2,4]triazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 2.54 g of 3-amino-1,2,4-triazole, 5.29 g of 3-dimethylamino-1-(3-pyridyl)-2-propene-1-one and 25 ml of glacial acetic acid was heated under reflux for 6 hours. The solvent was removed in vacuo and the solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane. The organic layer was separated and dried over powdered anhydrous sodium sulfate. This solution was passed through a short column of a hydrous magnesium silicate and the effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization was noted. On cooling the desired compound was separated and collection by filtration gave 1.95 g. of colorless crystals mp. 209°-210° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 6 hours
  3. customThe solvent was removed in vacuo
  4. customthe solid residue was partitioned between a saturated aqueous sodium bicarbonate solution and dichloromethane
  5. customThe organic layer was separated
  6. customdried
  7. temperaturethe effluent was refluxed on a steam bath with the gradual addition of hexane until crystallization
  8. temperatureOn cooling the desired compound
  9. customwas separated
  10. customcollection
  11. filtrationby filtration
  12. customgave 1.95 g

Sources & evidence

ORD record
ord-71b0cc88388149b8b5c31ae457814789
Source dataset
uspto-grants-1984_04
Patent number
US04444774

Linked notes

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