N-bromobutanimide → 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 2426106Notes

Reaction equation

HRID 2426106 reaction equation
[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.[Br:13]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Br:13][CH2:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[Cl:1])[N:8]([CH3:12])[N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 131255724-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 575815813-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To a solution of 4-chloro-1,3-dimethyl-1H-pyrazolo[3,4-d]pyrimidine (752 mg, 4.12 mmol, Example 4) in carbon tetrachloride (45 mL) were added N-bromosuccinimide (964.4 mg, 5.36 mmol, Aldrich) and AlBN (209.6 mg, 1.25 mmol, Aldrich). The mixture was heated at reflux for 7 hours. The resulting reaction mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 95/5 to 70/30) to give 3-bromomethyl-4-chloro-1-methyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid. (Yield 941.3 mg).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 7 hours
  3. customThe resulting reaction mixture
  4. concentrationwas concentrated under reduced pressure
  5. customthe residue was purified by flash chromatography (silica gel, hexanes-ethyl acetate, 95/5 to 70/30)

Sources & evidence

ORD record
ord-d50da4a33e9246bbbac6e0beb7e0d5ea
Source dataset
uspto-grants-2011_06
Patent number
US07968554B2

Reaction notes

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