Benzoylacetone → 5-Methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

HRID 653571

Reaction equation

HRID 653571 reaction equation
[NH2:1][C:2]1[N:6]=[C:5]([NH2:7])[NH:4][N:3]=1.[C:8]([CH2:16][C:17](=O)[CH3:18])(=O)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>C(O)(=O)C>[CH3:18][C:17]1[CH:16]=[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[N:3]2[N:4]=[C:5]([NH2:7])[N:6]=[C:2]2[N:1]=1

Participants

4

Reactant 2

HCID 7166BenzoylacetoneHCID 150783,5-Diamino-1,2,4-triazole

Product 1

HCID 9757135-Methyl-7-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-2-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 14 g (141.4 mmol) of 3,5-diamino-1,2,4-triazole and 24.0 g (148.1 mmol) benzoylacetone was heated in 200 ml of glacial acetic acid at reflux for 2 hours. A solution soon formed after heating. The solvent was removed in vacuo and the residue dissolved in 400 ml of methylene chloride which was then washed with water (2X), brine and dried over magnesium sulfate. The solution was concentrated in vacuo (not to complete dryness) and ethyl acetate added to the residue. The precipitated solid was filtered and washed with ethyl acetate to give 16.0 g of reasonably pure intermediate 5-methyl-7-phenyl-1,2,4-triazolo[1,5-a]pyrimidin-2-amine which was able to be taken on directly to the next step without further purification m.p. 246°-250° .

Workup

  1. temperatureat reflux for 2 hours
  2. customA solution soon formed
  3. temperatureafter heating
  4. customThe solvent was removed in vacuo
  5. dissolutionthe residue dissolved in 400 ml of methylene chloride which
  6. washwas then washed with water (2X), brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationThe solution was concentrated in vacuo (not to complete dryness) and ethyl acetate
  9. additionadded to the residue
  10. filtrationThe precipitated solid was filtered
  11. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-b7ff368a79f44b32811312565bf9f670
Source dataset
uspto-grants-1992_07
Patent number
US05127936

Linked notes

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