6-phenyl-1,2,4-triazine-3,5(2h,4h)-dione → HCID 22313051, compound

HRID 965633Notes

Reaction equation

HRID 965633 reaction equation
[C:1]1([C:7]2[C:8](=[O:14])[NH:9][C:10](=[O:13])[NH:11][N:12]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si](C([Si](C)(C)C)C(N)=O)(C)C.[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH2:30]Br>C(#N)C>[F:27][C:28]1[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[C:29]=1[CH2:30][N:11]1[C:10](=[O:13])[NH:9][C:8](=[O:14])[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:12]1

Participants

5

Reactant 3

HCID 2533636-phenyl-1,2,4-triazine-3,5(2h,4h)-dioneHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 11708267Bistrimethylsilylacetamid

Product 1

HCID 22313051HCID 22313051, compoundYield 88.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

To a stirring suspension of 6-phenyl-1,2,4-triazine-3,5-(2H,4H)-dione (6.00 g, 31.7 mmol) in dry acetonitrile (50 mL) under nitrogen was added bis(trimethylsilyl)acetamide (15.7 mL, 63.4 mmol). The resulting yellow solution was heated at 80° C. for 3 hours. The solution was cooled and 2,6-difluorobenzyl bromide (8.20 g, 39.6 mmol) was added in one portion. The mixture was heated at 80° C. under nitrogen for an additional 15 hours. The resulting solution was cooled to room temperature, quenched with methanol (20 mL), and diluted with dichloromethane (175 mL). The mixture was washed with water (75 mL) and brine (70 mL), and dried over magnesium sulfate. Evaporation gave a tan solid that was triturated with cold diethyl ether (5×5 mL). After drying in vacuo, the compound was isolated as a flocculent, off-white solid (8.80 g, 88%).

Workup

  1. temperatureThe solution was cooled
  2. temperatureThe mixture was heated at 80° C. under nitrogen for an additional 15 hours
  3. temperatureThe resulting solution was cooled to room temperature
  4. customquenched with methanol (20 mL)
  5. additiondiluted with dichloromethane (175 mL)
  6. washThe mixture was washed with water (75 mL) and brine (70 mL)
  7. dry with materialdried over magnesium sulfate
  8. customEvaporation
  9. customgave a tan solid
  10. customthat was triturated with cold diethyl ether (5×5 mL)
  11. customAfter drying in vacuo

Sources & evidence

ORD record
ord-78f9c3be1f074e14a6b87f76a9b6e296
Source dataset
uspto-grants-2005_10
Patent number
US06951858B2

Reaction notes

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