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

HRID 1453212Notes

Reaction equation

HRID 1453212 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH2:7][OH:8])[N:3]=1.[CH3:9][C:10](=O)[CH2:11][C:12](=O)[CH3:13]>C(O)(=O)C>[CH3:9][C:10]1[CH:11]=[C:12]([CH3:13])[N:6]2[N:5]=[C:4]([CH2:7][OH:8])[N:3]=[C:2]2[N:1]=1

Participants

4

Reactant 2

HCID 31261AcetylacetoneHCID 178508559HCID 178508559, compound

Product 1

HCID 44141733(5,7-Dimethyl-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)methanolYield 95%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of (5-amino-1H-[1,2,4]triazol-3-yl)-methanol (9.5 g, 50 mmol) from Step 1 above in acetic acid (200 mL) was added 2,4-pentanedione (5.13 mL, 50 mmol). The mixture was heated to reflux for 4 hours, and then cooled to room temperature. The product was isolated by removing the solvent by rotary evaporation (8.5 g, 95% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 4 hours
  3. customThe product was isolated
  4. customby removing the solvent
  5. customby rotary evaporation (8.5 g, 95% yield)

Sources & evidence

ORD record
ord-cdab1387e6b042a79de1d6116b59c852
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

Loading…