Sodium hydride → HCID 59298833, compound

HRID 2234859Notes

Reaction equation

HRID 2234859 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.O>[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

6

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 59298833HCID 59298833, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

0.85 g (21.3 mmol) of NaH (60% in paraffin) is 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 added dropwise. The reaction medium is stirred for 1 h at ambient temperature and then 5 g (21.3 mmol) of 1,1,1-trifluoro-4-iodo-butane are added; stirring is then continued for 3 h at ambient temperature. After dry concentration, the residue obtained is taken up in H2O and extracted with ethyl acetate. After drying on MgSO4, the organic phases are evaporated and the oil obtained is purified by flash chromatography on silica (petroleum ether:AcOEt 80:20). 5.3 g of crystals corresponding to compound 4a are isolated (yield=87%). TLC silica gel 60 F 254 Merck, petroleum ether:AcOEt 70:30, Rf=0.58.

Workup

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

Sources & evidence

ORD record
ord-ea092a75b816412bad65e21fc006aa1d
Source dataset
uspto-grants-2010_05
Patent number
US07713971B2

Reaction notes

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