Methyl iodide → 3-Bromo-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 1396579Notes

Reaction equation

HRID 1396579 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:12])=[N:8][C:9]=2[Cl:11])[NH:4][N:3]=1.[OH-].[K+].[CH3:15]I>CN(C=O)C.O.CCOC(C)=O>[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([NH2:12])=[N:8][C:9]=2[Cl:11])[N:4]([CH3:15])[N:3]=1

Participants

7

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 178508433HCID 178508433, compound

Product 1

HCID 713077513-Bromo-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (580 mg, 2.3 mmol) is dissolved in DMF (40 ml), potassium hydroxide (131 mg, 2.3 mmol) is added and the reaction mixture is stirred at room temperature for 15 minutes. Methyl iodide (0.133 ml, 2.3 mmol) is then added and the reaction is continued stirring overnight. The reaction mixture is diluted with water (60 ml) and EtOAc (60 ml), the layers are separated and the organic portion is washed with brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound.

Workup

  1. stirringthe reaction is continued stirring overnight
  2. customthe layers are separated
  3. washthe organic portion is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7401b843f0564c118f89273a19d0b61d
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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