Trifluoroacetic acid → 3-(2-fluoro-4-phenoxyphenyl)-1-(3R)-3-piperidinyl-1H-Pyrazolo[3,4-d]pyrimidin-4-amine

HRID 1854949Notes

Reaction equation

HRID 1854949 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@@H:25]3[CH2:30][CH2:29][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.FC(F)(F)C(O)=O>ClCCl>[F:24][C:12]1[CH:13]=[C:14]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:16][C:11]=1[C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[NH2:1])[N:8]([C@@H:25]2[CH2:30][CH2:29][CH2:28][NH:27][CH2:26]2)[N:9]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86714497tert-butyl (3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate

Product 1

HCID 710152843-(2-fluoro-4-phenoxyphenyl)-1-(3R)-3-piperidinyl-1H-Pyrazolo[3,4-d]pyrimidin-4-amineYield 74.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Into a 100 mL round-bottom flask, was placed a solution of tert-butyl (3R)-3-[4-amino-3-(2-fluoro-4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]piperidine-1-carboxylate (320 mg, 0.63 mmol, 1.00 equiv) in dichloromethane (50 mL). This was followed by the addition of trifluoroacetic acid (10 mL) dropwise with stirring. The resulting solution was stirred overnight at room temperature and then concentrated under vacuum. The residue was diluted with water and the pH value of the solution was adjusted to >7 with sodium carbonate. The resulting solution was extracted with dichloromethane and the organic layers combined and dried over anhydrous sodium sulfate and concentrated under vacuum to give 190 mg (74%) of 3-(2-fluoro-4-phenoxyphenyl)-1-[(3R)-piperidin-3-yl]-1H-pyrazolo[3,4-d]pyrimidin-4-amine as a brown solid.

Workup

  1. customInto a 100 mL round-bottom flask, was placed
  2. stirringThe resulting solution was stirred overnight at room temperature
  3. concentrationconcentrated under vacuum
  4. additionThe residue was diluted with water
  5. extractionThe resulting solution was extracted with dichloromethane
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-b84aa85f48904ab2bce9d369079df0a0
Source dataset
uspto-grants-2015_02
Patent number
US08962831B2

Reaction notes

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