Sodium hydride → 6-Bromo-4-methyl-2-(4,4,4-trifluoro-butyl)-2H-[1,2,4]triazine-3,5-dione

HRID 1917087Notes

Reaction equation

HRID 1917087 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:5](=[O:12])[N:6]([CH3:11])[C:7](=[O:10])[NH:8][N:9]=1.[F:13][C:14]([F:20])([F:19])[CH2:15][CH2:16][CH2:17]I>CN(C=O)C>[Br:3][C:4]1[C:5](=[O:12])[N:6]([CH3:11])[C:7](=[O:10])[N:8]([CH2:17][CH2:16][CH2:15][C:14]([F:20])([F:19])[F:13])[N:9]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2605646-bromo-4-methyl-1,2,4-triazine-3,5(2h,4h)-dioneHCID 27751891,1,1-Trifluoro-4-iodobutane

Product 1

HCID 592988336-Bromo-4-methyl-2-(4,4,4-trifluoro-butyl)-2H-[1,2,4]triazine-3,5-dioneYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

0.85 g (21.3 mmol) of NaH (at 60% in paraffin) are placed in 10 mL of DMF under nitrogen. A solution of 4 g (19.4 mmol) of intermediate 2a in 40 mL of DMF is poured dropwise. The reaction medium is stirred for 1 h at room temperature and then 5 g (21.3 mmol) of 1,1,1-trifluoro-4-iodo-butane are added dropwise, and stirring is then continued for 3 h at room temperature. After dry concentration, the obtained residue is taken up with H2O and extracted with ethyl acetate. After drying on MgSO4, the organic phases are evaporated and the obtained oil is purified by flash chromatography on silica (petroleum ether-AcOEt: 80-20). 5.3 g of crystals corresponding to the compound 4a (yield=87%) are isolated.

Workup

  1. stirringstirring
  2. waitis then continued for 3 h at room temperature
  3. customAfter dry
  4. concentrationconcentration
  5. extractionextracted with ethyl acetate
  6. customAfter drying on MgSO4
  7. customthe organic phases are evaporated
  8. customthe obtained oil is purified by flash chromatography on silica (petroleum ether-AcOEt: 80-20)

Sources & evidence

ORD record
ord-e6259a56657a4e089119092fe5643e23
Source dataset
uspto-grants-2013_12
Patent number
US08618287B2

Reaction notes

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