Methyl iodide → 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 2426105Notes

Reaction equation

HRID 2426105 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[C:10]([CH3:11])[C:3]=12.[C:12](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH3:12])[N:9]=[C:10]([CH3:11])[C:3]=12

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178434472HCID 178434472, compound

Product 1

HCID 131255724-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 4-chloro-3-methyl-1H-pyrazolo[3,4-d]pyrimidine (150.4 mg, 0.89 mmol, Example 3) and potassium carbonate (187 mg, 1.35 mmol) in dimethylformamide (6 mL) was added iodomethane (225 mg, 1.59 mmol, Aldrich). The reaction mixture was stirred at room temperature for 2 hours before it was diluted with ethyl acetate, washed with water, brine, dried and concentrated. The crude product was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40) to give 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 162.3 mg).

Workup

  1. washwashed with water, brine
  2. customdried
  3. concentrationconcentrated
  4. customThe crude product was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 90/10 to 60/40)

Sources & evidence

ORD record
ord-1534ab724aa8403085dbf0bcbf542ab2
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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