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

HRID 2056096Notes

Reaction equation

HRID 2056096 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][CH2:15][N:14](C(OC(C)(C)C)=O)[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][CH2:15][NH:14][CH2:13]2)[N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22346738tert-butyl (3R)-3-{4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl}piperidine-1-carboxylate

Product 1

HCID 223471203-iodo-1-(3-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
45 °C

Procedure

To a mixture of tert-butyl 3-(4-amino-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (1.2 g, 0.0027 mol) in acetone (20 mL) was added an aqueous 6N solution of hydrogen chloride (8 mL) at room temperature. The mixture was stirred at 45° C. for 1.5 hours, and then room temperature for 16 hours. The precipitate was filtered and washed with acetone. The solid was dried to give 3-iodo-1-(3-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-4-amine dihydrochloride (1 g, 0.0024 mol). TLC (methanol/dichloromethane=5:95) Rf 0.14 MS: MH+ 345

Workup

  1. waitroom temperature for 16 hours
  2. filtrationThe precipitate was filtered
  3. washwashed with acetone
  4. customThe solid was dried

Sources & evidence

ORD record
ord-30bb236ecb9a43d489d4b6dab9b9fe9e
Source dataset
uspto-grants-2008_02
Patent number
US07332497B2

Reaction notes

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