Methyl iodide → 3-(4-Chloro-indazol-1-yl)-1-methyl-6-trifluoromethylpyrimidine-2,4-dione

HRID 842543Notes

Reaction equation

HRID 842543 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]1=[O:22].[C:23](=O)([O-])[O-].[K+].[K+].CI>C(#N)C>[Cl:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[N:11]1[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[N:13]([CH3:23])[C:12]1=[O:22]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 226142623-(4-chloro-indazol-1-yl)-6-trifluoromethyl-1H-pyrimidine-2,4-dione

Product 1

HCID 114507933-(4-Chloro-indazol-1-yl)-1-methyl-6-trifluoromethylpyrimidine-2,4-dioneYield 39.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 168B (100 mg, 0.3 mmol), dry acetonitril (3 mL), potassium carbonate (0.05 g, 0.33 mmol) and methyl iodide (0.1 g, 0.7 mmol) is stirred overnight at room temperature. The solids are removed by filtration. The motherliquor is concentrated under reduced pressure. The residue obtained is purified by flash chromatography (ethyl acetate/petrol ether 3/7) which yields the product as an orange semi-solid (41 mg).

Workup

  1. customThe solids are removed by filtration
  2. concentrationThe motherliquor is concentrated under reduced pressure
  3. customThe residue obtained
  4. customis purified by flash chromatography (ethyl acetate/petrol ether 3/7) which

Sources & evidence

ORD record
ord-9c1a77e972fb40a085e49424b87461d6
Source dataset
uspto-grants-2002_04
Patent number
US06376426B1

Reaction notes

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