Pyridine → 6-bromo-4-methyl-2-o-tolyl-2H-[1,2,4]triazine-3,5-dione

HRID 1917089Notes

Reaction equation

HRID 1917089 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[NH:6][N:7]=1.N1C=CC=CC=1.[C:17]1([CH3:26])[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[C:5](=[O:8])[N:6]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][C:17]=2[CH3:26])[N:7]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 2605646-bromo-4-methyl-1,2,4-triazine-3,5(2h,4h)-dioneHCID 27332672-Methylphenyl boronic acid

Product 1

HCID 582697586-bromo-4-methyl-2-o-tolyl-2H-[1,2,4]triazine-3,5-dioneYield 75%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

0.5 g (2.43 mmol) of intermediate 2a are placed in the presence of 0.4 mL (4.85 mmol) of pyridine, 0.66 g (4.85 mmol) of o-tolyl boronic acid, 0.66 g (3.64 mmol) of copper acetate in 50 mL of CH2Cl2. The reaction medium is stirred for 24 h at room temperature and then filtered on celite. The filtrate is washed with water, and then with 0.01N hydrochloric acid. After drying on MgSO4, the organic phase is dry concentrated. After washing the obtained residue with diethyl ether, 0.54 g of a white solid corresponding to the compound 41 are isolated (yield 75%)

Workup

  1. filtrationfiltered on celite
  2. washThe filtrate is washed with water
  3. customAfter drying on MgSO4
  4. customthe organic phase is dry
  5. concentrationconcentrated
  6. washAfter washing the obtained residue with diethyl ether, 0.54 g of a white solid corresponding to the compound 41
  7. customare isolated (yield 75%)

Sources & evidence

ORD record
ord-5a995bddab3044f694c4664d26f44fd0
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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