3,5-Heptanedione → 5,7-Diethyl-2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidine

HRID 1752796Notes

Reaction equation

HRID 1752796 reaction equation
[CH3:1][CH2:2][C:3](=O)[CH2:4][C:5](=O)[CH2:6][CH3:7].[NH2:10][C:11]1[N:15]=[C:14]([S:16][CH3:17])[NH:13][N:12]=1>C(O)(=O)C>[CH2:2]([C:3]1[CH:4]=[C:5]([CH2:6][CH3:7])[N:12]2[N:13]=[C:14]([S:16][CH3:17])[N:15]=[C:11]2[N:10]=1)[CH3:1]

Participants

4

Reactant 2

HCID 819233,5-HeptanedioneHCID 178503514HCID 178503514, compound

Product 1

HCID 867193195,7-Diethyl-2-(methylsulfanyl)-[1,2,4]triazolo[1,5-a]pyrimidineYield 88%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
135 °C

Procedure

A mixture of 3,5-heptanedione (9.85 g, 76.8 mmol), 3-amino-5-methylthio-1H-1,2,4-triazole (10.0 g, 76.8 mmol), and glacial acetic acid (60 mL) was added to a 200 mL RBF with a magnetic stirring bar. The flask was fitted with a condenser, and warmed in an oil bath to a gentle reflux at 135° C. The mixture was heated for 24 hours. Progress of the reaction was monitored by analytical HPLC with UV detection at 215 and 254 nm. The starting material 3-amino-5-methylthio-1H-1,2,4-triazole eluted rapidly with retention time of 0.7 min, and the product eluted with retention time of 4.7 min. The mixture was cooled to room temperature, then slowly poured into stirring ice/water (800 mL) to precipitate product and stirred ˜20 minutes. Solids were isolated by filtration, rinsed with water (200 mL), and then dried under reduced pressure to afford the title compound as a powder (15.0 g, 88% yield).

Workup

  1. additionwas added to a 200 mL RBF with a magnetic stirring bar
  2. customThe flask was fitted with a condenser
  3. temperaturewarmed in an oil bath to
  4. temperatureThe mixture was heated for 24 hours
  5. washThe starting material 3-amino-5-methylthio-1H-1,2,4-triazole eluted rapidly with retention time of 0.7 min
  6. washthe product eluted with retention time of 4.7 min
  7. temperatureThe mixture was cooled to room temperature
  8. additionslowly poured
  9. customto precipitate product
  10. stirringstirred ˜20 minutes
  11. customSolids were isolated by filtration
  12. washrinsed with water (200 mL)
  13. customdried under reduced pressure

Sources & evidence

ORD record
ord-0731c6b706e34c9b8bfd0845c401823c
Source dataset
uspto-grants-2015_10
Patent number
US09163027B2

Reaction notes

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