Water → 6-chloro-1H-pyrazolo[3,4-d]pyrimidine

HRID 750483Notes

Reaction equation

HRID 750483 reaction equation
[NH2:1][NH2:2].[Cl:3][C:4]1[N:9]=[C:8](Cl)[C:7]([CH:11]=O)=[CH:6][N:5]=1.O>C1COCC1>[Cl:3][C:4]1[N:9]=[C:8]2[NH:1][N:2]=[CH:11][C:7]2=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9321HydrazineHCID 189831682,4-Dichloropyrimidine-5-carbaldehyde

Product 1

HCID 529112546-chloro-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of hydrazine (Aldrich, 64 mg, 2 mmol) in THF (5 mL), 2,4-Dichloro-pyrimidine-5-carbaldehyde (Example 17, 176 mg, 1 mmol) was added and the mixture was stirred at room temperature for 30 min. The mixture was poured into water and extracted with EtOAc. The extract was dried with sodium sulfate and the solvent was removed to give an orange solid. 128 mg, 82%. MS (M+H)+, 155.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe extract was dried with sodium sulfate
  3. customthe solvent was removed
  4. customto give an orange solid

Sources & evidence

ORD record
ord-d7915d3b22ff4823aa12afe4cc5ad059
Source dataset
uspto-grants-2008_07
Patent number
US07405220B2

Reaction notes

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