Methyl iodide → HCID 22028116, compound

HRID 983439Notes

Reaction equation

HRID 983439 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:15]=[C:14]([Cl:16])[N:13]=[CH:12][N:11]=2)[CH:5]=[CH:6][C:7]=1[F:8].[CH3:17]I.[H-].[Na+]>CN(C=O)C>[CH3:17][N:13]1[CH:12]=[N:11][C:10]([NH:9][C:4]2[CH:5]=[CH:6][C:7]([F:8])=[C:2]([Cl:1])[CH:3]=2)=[N:15][CH:14]1[Cl:16]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22028114HCID 22028114, compound

Product 1

HCID 22028116HCID 22028116, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of (3-chloro-4-fluoro-phenyl)-(4-chloro-[1,3,5]triazin-2-yl)-amine (1.7 g, 6.56 mmol) and MeI (1.5 mL) in DMF (20 mL) under a nitrogen atmosphere was added NaH (60% dispersion, 0.53 mg, 13.3 mmol). The mixture was stirred for 3 h. The reaction was quenched by the addition of water and the organic extracts are taken up in EtOAc, dried over anh. MgSO4 and concentrated under reduced pressure. The crude product was purified via medium pressure liquid chromatography using CH2Cl2 as the solvent system to give N-methyl-2-chloro-4-(3-chloro-4-fluoroanilino)-1,3,5-triazine.

Workup

  1. customThe reaction was quenched by the addition of water
  2. dry with materialdried over anh. MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified via medium pressure liquid chromatography

Sources & evidence

ORD record
ord-ccf80b7f9e6242cf81015ba63791a8f3
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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