Acetic Acid → 4-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine

HRID 1062819Notes

Reaction equation

HRID 1062819 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.[C:12](O)(=[O:14])C>C[O-].[Na+]>[CH3:12][O:14][C:2]1[N:7]=[C:6]([NH2:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 117896254-chloro-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 112521974-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amineYield 99%

Reagents, catalysts & solvents 1

HCID 10942334Sodium MethoxideSolvent

Procedure

Compound 3 (70.4 g, 0.416 mol) was refluxed in methanolic sodium methoxide solution (25 g sodium dissolved in 1 L methanol) for 2 h. The reaction mixture was cooled to room temperature and neutralized by addition of acetic acid (75 ml). The mixture was evaporated to dryness and the solid was triturated in 600 ml of water, filtered and dried to provide 67.5 g (99% yield) of 4-methoxy-6-aminopyrazolo[3,4-d]pyrimidine (4).

Workup

  1. customThe mixture was evaporated to dryness
  2. customthe solid was triturated in 600 ml of water
  3. filtrationfiltered
  4. customdried

Sources & evidence

ORD record
ord-3142ad87d75e4854845801b740436dbc
Source dataset
uspto-grants-2005_11
Patent number
US06962991B2

Reaction notes

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