Pyridine → HCID 59496094, compound

HRID 1513328Notes

Reaction equation

HRID 1513328 reaction equation
C([N:4]1[C:9](=[O:10])[NH:8][C:7](=[O:11])[C:6]([CH3:12])=[N:5]1)(=O)C.N1C=CC=CC=1.[C:19](Cl)(=[O:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O1CCOCC1>[CH3:12][C:6]1[C:7](=[O:11])[N:8]([C:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[O:26])[C:9](=[O:10])[NH:4][N:5]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 7412Benzoyl chloride2×HCID 44725398HCID 44725398, compound

Product 1

HCID 59496094HCID 59496094, compoundYield 67.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-acetyl-6-methyl-1,2,4-triazine-3,5(2H,4H)-dione (P1, 196 mg, 1.159 mmol) in 1,4-Dioxane (2 mL) and dry pyridine (0.281 mL, 3.48 mmol) at 5° C. was treated benzoyl chloride (0.155 mL, 1.333 mmol) was added dropwise, then the mixture was stirred at room temperature overnight. The day after 0.1 eq of Benzoyl chloride were added and the mixture stirred at rt for further 4 hours. The reaction mixture was then filtered to remove the piridinium salt and the solvents evaporated under vacuum. The residue was dissolved in EtOH (5 mL), then HCl 37% (126 μL) was added and the reaction was refluxed for 15 minutes. Solvent was evaporated under reduced pressure and the residue was purified by flash chromatography (eluent: DCM to DCM/MeOH 6:4) providing the title compound 6-methyl-4-(phenylcarbonyl)-1,2,4-triazine-3,5(2H,4H)-dione (180 mg, 0.779 mmol, 67% yield).

Workup

  1. additionwas added dropwise
  2. stirringthe mixture stirred at rt for further 4 hours
  3. filtrationThe reaction mixture was then filtered
  4. customto remove the piridinium salt
  5. customthe solvents evaporated under vacuum
  6. dissolutionThe residue was dissolved in EtOH (5 mL)
  7. additionHCl 37% (126 μL) was added
  8. temperaturethe reaction was refluxed for 15 minutes
  9. customSolvent was evaporated under reduced pressure
  10. customthe residue was purified by flash chromatography (eluent: DCM to DCM/MeOH 6:4)

Sources & evidence

ORD record
ord-5f75877c1d784dab83255a46f527e3a9
Source dataset
uspto-grants-2012_07
Patent number
US08217168B2

Reaction notes

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