Hydrochloric Acid → 3-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride

HRID 432370Notes

Reaction equation

HRID 432370 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:12]3[CH2:17][CH2:16][N:15](C(OC(C)(C)C)=O)[CH2:14][CH2:13]3)[N:9]=[C:10]([I:11])[C:3]=12.[ClH:25]>CC(C)=O>[ClH:25].[ClH:25].[I:11][C:10]1[C:3]2[C:4](=[N:5][CH:6]=[N:7][C:2]=2[NH2:1])[N:8]([CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22346822tert-Butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidine-1-carboxylate

Product 1

HCID 223473623-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

The crude tert-butyl 4-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (69.4 g, 156.30 mmol) was dissolved in acetone (900 mL) and 6N aqueous hydrochloric acid (300 mL) was slowly added dropwise. The reaction was then heated at 45° C. which yielded a precipitate. After 1.5 hours, the precipitate was collected by vacuum filtration, washed with minimal acetone and dried on the lyophilizer to yield 3-iodo-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride salt as a yellow solid (16.61 g, 39.8 mmol). HPLC-RT: 6.16 min. (flow rate: 1 mL/min λ=254 nm Gradient: 5% to 85% acetonitrile/0.1M aqueous ammonium acetate gradient over 20 min.; Deltapak C18, 300A, 5 μm, 150×3.9 mm column); m/z (MH+)=345.0.

Workup

  1. customyielded a precipitate
  2. filtrationthe precipitate was collected by vacuum filtration
  3. washwashed with minimal acetone
  4. customdried on the lyophilizer

Sources & evidence

ORD record
ord-5db5b41bb27f4cc5aadee1f6c68a5a06
Source dataset
uspto-grants-2003_12
Patent number
US06660744B1

Reaction notes

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