Water → HCID 117728446, compound

HRID 1778443Notes

Reaction equation

HRID 1778443 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:25]3[CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][C:12]=3[F:24])[C:3]=12.CCOC(C)=O.O>C(O)(C(F)(F)F)=O>[NH:27]1[CH2:26][CH:25]([N:8]2[C:4]3=[N:5][CH:6]=[N:7][C:2]([NH2:1])=[C:3]3[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:13][C:12]=3[F:24])=[N:9]2)[CH2:28]1

Participants

5

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 90003214HCID 90003214, compound

Product 1

HCID 117728446HCID 117728446, compoundYield 94.9%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl 3-(4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)azetidine-1-carboxylate (800 mg) in TFA (8 mL) was stirred for 1 hour. To the residue was added EtOAc and 1 water and the layers were separated. The aqueous layer was extracted with EtOAc and the combined organic layer was evaporated to around 50 ml and washed with 2M HCl. The combined aqueous layer was adjusted with NaOH to pH 8-9, extracted with EtOAc and the combined organic layer washed with brine, and dried over Na2SO4. The solvent was removed to obtain 600 mg of 1-(azetidin-3-yl)-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customthe combined organic layer was evaporated to around 50 ml
  4. washwashed with 2M HCl
  5. extractionextracted with EtOAc
  6. washthe combined organic layer washed with brine
  7. dry with materialdried over Na2SO4
  8. customThe solvent was removed

Sources & evidence

ORD record
ord-e0ef154ca6e44a66b4de47200841ba6d
Source dataset
uspto-grants-2016_02
Patent number
US09266895B2

Reaction notes

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