Hydrochloric Acid → 4-(1-Piperazinyl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride

HRID 1192437Notes

Reaction equation

HRID 1192437 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][N:17]=[C:16]3[NH:20][N:21]=[CH:22][C:15]=23)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:23]>O1CCOCC1.C(OCC)C>[ClH:23].[ClH:23].[N:11]1([C:14]2[N:19]=[CH:18][N:17]=[C:16]3[NH:20][N:21]=[CH:22][C:15]=23)[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 11472214tert-Butyl 4-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)piperazine-1-carboxylate

Product 1

HCID 675398394-(1-Piperazinyl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochlorideYield 99%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent2×

Procedure

The 4-(1H-pyrazolo[3,4-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (600 mg, 1.97 mmol) was dissolved in 4 mL of 1,4-dioxane and treated with 10 mL of 4M HCl in 1,4-dioxane at room temperature. The solution was allowed to stir for two hours to afford a light-yellow suspension of product. The solvent was diluted with diethyl ether, stirred for ten minutes, and filtered. The pad of product was washed with diethyl ether and allowed to dry under a stream of nitrogen to give the 4-piperazin-1-yl-1H-pyrazolo[3,4-d]pyrimidine bis-hydrochloride salt as a light-yellow solid (539 mg, 99%). 1H NMR (D6O, 400 MHz) δ 8.59 (s, 1H), 8.42 (s, 1H), 4.29 (appt, J=5.6 Hz, 4H), 3.42 (appt, J=5.6 Hz, 4H). LCMS (APCI+) m/z 205 [M+H]+; Rt=0.34 min.

Workup

  1. customto afford
  2. additiona light-yellow suspension of product
  3. stirringstirred for ten minutes
  4. filtrationfiltered
  5. washThe pad of product was washed with diethyl ether
  6. customto dry under a stream of nitrogen

Sources & evidence

ORD record
ord-4580b13dd05f4905a1b42d7cfb9c84c9
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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