1,4-Dioxane hydrochloride → 7-Benzenesulfonyl-4-piperazin-1-yl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride

HRID 1192360Notes

Reaction equation

HRID 1192360 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[C:15]3[C:22]([C:23]4[S:24][CH:25]=[CH:26][CH:27]=4)=[CH:21][N:20]([S:28]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)(=[O:30])=[O:29])[C:16]=3[N:17]=[CH:18][N:19]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.[ClH:37].O1CCOCC1>O1CCOCC1.CCOCC>[ClH:37].[ClH:37].[C:31]1([S:28]([N:20]2[C:16]3[N:17]=[CH:18][N:19]=[C:14]([N:11]4[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]4)[C:15]=3[C:22]([C:23]3[S:24][CH:25]=[CH:26][CH:27]=3)=[CH:21]2)(=[O:30])=[O:29])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 2

HCID 204431481,4-Dioxane hydrochlorideHCID 675390164-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 675387477-Benzenesulfonyl-4-piperazin-1-yl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochlorideYield 95%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of 4-(7-Benzenesulfonyl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (120 mg, 0.23 mmol) in 2 mL dioxane was added 1.5 mL 4M HCl/dioxane. The reaction mixture was stirred at room temperature 6 hours, after which it was diluted with ether, and the solids were isolated by filtration through a fritted funnel with nitrogen pressure, rinsed with ether, and dried in vacuo to give 7-Benzenesulfonyl-4-piperazin-1-yl-5-thiophen-2-yl-7H-pyrrolo[2,3-d]pyrimidine dihydrochloride (110 mg, 95%) as a yellow powder. LCMS (APCI+) m/z 426 [M+H]+; Rt: 1.95 min.

Workup

  1. customthe solids were isolated by filtration through a fritted funnel with nitrogen pressure
  2. washrinsed with ether
  3. customdried in vacuo

Sources & evidence

ORD record
ord-a2ded21bf24344caa1266ecda88851f4
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

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