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Triethylamine → 5-Bromo-2-(4-(phenylsulfonyl)-1-piperazinyl)pyrimidine

HRID 1972368
Notes
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Reaction equation

HRID 1972368 reaction equation
Cl.[C:2]1([S:8]([N:11]2[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)(=[O:10])=[O:9])[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17][C:18]1[CH:19]=[N:20][C:21](Cl)=[N:22][CH:23]=1.O1CCOCC1.C(N(CC)CC)C>O>[Br:17][C:18]1[CH:19]=[N:20][C:21]([N:14]2[CH2:15][CH2:16][N:11]([S:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)(=[O:10])=[O:9])[CH2:12][CH2:13]2)=[N:22][CH:23]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 312751,4-DioxaneHCID 6066655-Bromo-2-chloropyrimidineHCID 27565811-(Benzenesulfonyl)piperazine hydrochloride

Product 1

HCID 396606145-Bromo-2-(4-(phenylsulfonyl)-1-piperazinyl)pyrimidineYield 50.5%

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A 250 mL round-bottomed flask was charged with 1-(phenylsulfonyl)piperazine hydrochloride (4.08 g, 15.51 mmol, Example 15, step 1), 5-bromo-2-chloropyrimidine (2.50 g, 12.92 mmol, Sigma-Aldrich, St. Louis, Mo.), and 20 mL of dioxane. To this was added triethylamine (4.50 mL, 32.3 mmol). After stirring at room temperature for 3 h, the mixture was diluted with water (50 mL) and the resulting precipitate was collected by filtration to give 5-bromo-2-(4-(phenylsulfonyl)-1-piperazinyl)pyrimidine (2.50 g) as a white solid.

Workup

  1. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-143ebc81d7de4196acfd56839e71b66e
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08431563B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes