Acetylacetone → (5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

HRID 858735Notes

Reaction equation

HRID 858735 reaction equation
C([O:5][CH2:6][C:7]1[N:11]=[C:10]([NH2:12])[NH:9][N:8]=1)(=O)CO.[CH3:13][C:14]([CH2:16][C:17]([CH3:19])=O)=O>CCO.CC(O)=O>[CH3:13][C:14]1[CH:16]=[C:17]([CH3:19])[N:9]2[N:8]=[C:7]([CH2:6][OH:5])[N:11]=[C:10]2[N:12]=1

Participants

5

Reactant 2

HCID 31261AcetylacetoneHCID 178508532HCID 178508532, compound

Product 1

HCID 44141733(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanol

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
5 °C

Procedure

The title compound was prepared by a slight modification of a reported procedure (Lippman, E.; Becker, V., Z. Chem., 1974, 14, 405): A solution of (5-amino-1H-1,2,4-triazol-3-yl)methanol glycolate (30.7 g, 0.161 mol, from Step 1, above) and 2,4-pentadione (32.3 g, 0.323 mol, 2 equiv) in a mixture of EtOH (750 mL) and AcOH (250 mL) was refluxed 20 h. At the beginning the reaction mixture was clear solution, then gradually turned yellow towards the end of the heating period. The solvent was removed under reduced pressure, and the resulting yellow paste triturated with EtOH (100 mL) and stirred for 15 min. The slurry was chilled to 5° C. (ice bath) with stirring for 30 min, filtered, and washed with cold (0–5° C.) EtOH. The product was dried in vacuo at 25–30° C. to give 24 g (83.7%).

Workup

  1. temperaturewas refluxed 20 h
  2. customThe solvent was removed under reduced pressure
  3. customthe resulting yellow paste triturated with EtOH (100 mL)
  4. stirringwith stirring for 30 min
  5. filtrationfiltered
  6. washwashed with cold (0–5° C.) EtOH
  7. customThe product was dried in vacuo at 25–30° C.
  8. customto give 24 g (83.7%)

Sources & evidence

ORD record
ord-16bb9c84b1d742c2b62c61be9309e337
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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