Trifluoroacetic acid → 1-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine

HRID 897515Notes

Reaction equation

HRID 897515 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:24]3[CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25]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][CH:12]=3)[C:3]=12.FC(F)(F)C(O)=O>ClCCl>[NH:26]1[CH2:25][CH:24]([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:12]=[CH:13][C:14]([O:17][C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)=[CH:15][CH:16]=3)=[N:9]2)[CH2:27]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22346883tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanecarboxylate

Product 1

HCID 223471371-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amineYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-butyl 3-[4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl]-1-azetanecarboxylate (0.81 g, 0.0018 mol) in dichloromethane (5 mL) was slowly added a 20% solution of trifluoroacetic acid in dichloromethane (10 mL) at 0° C. under an atmosphere of nitrogen. The mixture was warmed to room temperature and stirred for eighteen hours. The solvent was removed under reduced pressure. An aqueous solution of 5 N sodium hydroxide was added to the residue to pH 11 at 0° C. The water phase was extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (1×60 mL) and brine (1×60 mL) and dried over sodium sulfate. The solvent was removed under reduced pressure to yield 1-(3-azetanyl)-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine (0.44 g, 0.0012 mol).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionAn aqueous solution of 5 N sodium hydroxide was added to the residue to pH 11 at 0° C
  3. extractionThe water phase was extracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with water (1×60 mL) and brine (1×60 mL)
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-1b5cff90f830485c88f5479aa272f825
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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