4-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine → 4-(3-chlorophenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride

HRID 1068894Notes

Reaction equation

HRID 1068894 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([N:18]4[CH2:23][CH2:22][N:21](C(OC(C)(C)C)=O)[CH2:20][CH2:19]4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1>O1CCOCC1.Cl.O1CCOCC1>[ClH:1].[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]3[NH:15][N:16]=[C:17]([N:18]4[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]4)[C:10]=23)[CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 211906074-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 211906574-(3-chlorophenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneSolventHCID 204431481,4-Dioxane hydrochlorideSolvent

Procedure

Under a nitrogen atmosphere, 2.0 g (4.65 mmol) of 4-(3-chloro-phenylamino)-3-(4-tert-butyloxycarbonyl-piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine (see Example 24) in 80 ml of dioxane and 80 ml of HCl/dioxane (4N) are stirred at 60° C. for 2 hours. Cooling and filtering yield 4-(3-chloro-phenylamino)-3-(piperazin-1-yl)-1H-pyrazolo[3,4-d]pyrimidine dihydrochloride; analysis calc. for C15H16N7Cl.2HCl (+0.14 H2O+5% dioxane): C44.93%, H 4.78%, N 22.97%, Cl 24.91%, H2O 0.68%; found C45.12%, H 4.73%, N 23.16%, Cl 24.67%, H2O 0.68%; HPLC: tRet(grad20-100/20)=8.0.

Workup

  1. temperatureCooling
  2. filtrationfiltering

Sources & evidence

ORD record
ord-5d9b1ed2dc4b477db8e43d891d64948d
Source dataset
uspto-grants-2001_06
Patent number
US06251911B1

Reaction notes

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