Triethylamine → 6-methyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 570523Notes

Reaction equation

HRID 570523 reaction equation
Cl[C:2]1[N:7]=[C:6]([CH3:8])[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]=12.C(N(CC)CC)C.[H][H].C(OCC)(=O)C>O1CCOCC1.[OH-].[OH-].[Pd+2]>[CH3:8][C:6]1[N:5]=[C:4]2[NH:9][N:10]=[CH:11][C:3]2=[CH:2][N:7]=1

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 8857Ethyl AcetateHCID 207959774-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidineHCID 178418361HCID 178418361, compound2×

Product 1

HCID 221154376-methyl-1H-pyrazolo[3,4-d]pyrimidine

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 312751,4-DioxaneSolvent

Procedure

4.464 g (approx. 24.28 mmol, purity 92%) of 4-chloro-6-methyl-1H-pyrazolo[3,4-d]pyrimidine were dissolved in 180 ml of dioxane, 2.948 g (29.14 mmol) of triethylamine and 5.629 g of 20% palladium hydroxide on carbon were added, and hydrogenation was effected with hydrogen at 3 bar and RT for 2 d. 100 ml of ethyl acetate, 2.948 g (29.14 mmol) of triethylamine and 2.000 g of 20% palladium hydroxide on carbon were added. The mixture was hydrogenated with hydrogen at 3 bar and RT for 3 h. The mixture was filtered through Celite and washed with a little dioxane/ethyl acetate, and the filtrate was concentrated on a rotary evaporator. 2.180 g (purity 73%, 49% of theory) of the target compound were obtained.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washwashed with a little dioxane/ethyl acetate
  3. concentrationthe filtrate was concentrated on a rotary evaporator
  4. custom2.180 g (purity 73%, 49% of theory) of the target compound were obtained

Sources & evidence

ORD record
ord-9bc69d50118643c787861db0f9d90b1e
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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