Water → HCID 117728446, compound

HRID 1429746Notes

Reaction equation

HRID 1429746 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-0c51246fc4e94fccb62e6aa8f73c00d3
Source dataset
uspto-grants-2015_01
Patent number
US08940744B2

Reaction notes

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