1,4-Cyclohexadiene → 4-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluoro-phenol

HRID 1396542Notes

Reaction equation

HRID 1396542 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:23]3[C:18](=[N:19][C:20]([NH2:24])=[N:21][CH:22]=3)[N:17]([CH3:25])[N:16]=2)=[CH:11][C:10]=1[F:26])C1C=CC=CC=1.C1CC=CCC=1>CCO.CC(O)=O.[Pd]>[NH2:24][C:20]1[N:19]=[C:18]2[N:17]([CH3:25])[N:16]=[C:15]([C:12]3[CH:13]=[CH:14][C:9]([OH:8])=[C:10]([F:26])[CH:11]=3)[C:23]2=[CH:22][N:21]=1

Participants

6

Reactant 2

HCID 123431,4-CyclohexadieneHCID 689679423-(4-Benzyloxy-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine

Product 1

HCID 1363872174-(6-Amino-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-2-fluoro-phenol

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

3-(4-Benzyloxy-3-fluoro-phenyl)-1-methyl-1H-pyrazolo[3,4-d]pyrimidin-6-ylamine (Example 35) (0.52 g, 1.49 mmol) is suspended in a mixture of EtOH and AcOH (5:1, 120 ml). The reaction mixture is degassed with argon before the addition of 10% palladium on activated charcoal (0.50 g) and 1,4-cyclohexadiene (1.4 ml, 14.88 mmol). The reaction mixture is heated at 80° C. overnight and filtered hot through Celite® (filter agent) washing copiously with MeOH (˜300 ml). The solvents are removed in vacuo and the resulting residue is triturated with EtOAc (˜20 ml) to afford the title compound as a white solid.

Workup

  1. filtrationfiltered hot through Celite® (filter agent)
  2. washwashing copiously with MeOH (˜300 ml)
  3. customThe solvents are removed in vacuo
  4. customthe resulting residue is triturated with EtOAc (˜20 ml)

Sources & evidence

ORD record
ord-d845ceda06c94bad9f1a9f6dcac417e6
Source dataset
uspto-grants-2014_12
Patent number
US08901134B2

Reaction notes

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