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

HRID 1192349Notes

Reaction equation

HRID 1192349 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[NH:8][N:9]=[CH:10][C:3]=12.C1C(=O)N([Br:18])C(=O)C1>C(Cl)(Cl)Cl>[Br:18][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[Cl:1])[NH:8][N:9]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 2210954-Chloro-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 1784783943-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidineYield 77%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a suspension of 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine (1.1 g, 7.1 mmol) in CHCl3 (50 mL) was added NBS (1.49 g, 8.4 mmol) The mixture was stirred at room temperature for 5 hours, cooled to 0 C and the solids were isolated by vacuum filtration, rinsed with cold CHCl3, and air dried. The solid was purified by column chromatography on silica (50% EtOAc/hexanes) to give 3-Bromo-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (1.3, 77%.)

Workup

  1. temperaturecooled to 0 C
  2. customthe solids were isolated by vacuum filtration
  3. washrinsed with cold CHCl3, and air
  4. customdried
  5. customThe solid was purified by column chromatography on silica (50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-d0623c7ee410495b94715e0a64356ee4
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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