Triethylamine → 2-Bromo-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanone

HRID 68553

Reaction equation

HRID 68553 reaction equation
[Br:1][CH2:2][C:3](Br)=[O:4].[N:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.C(N(CC)CC)C>C1COCC1>[Br:1][CH2:2][C:3]([N:15]1[CH2:16][CH2:17][N:12]([C:7]2[N:6]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH2:13][CH2:14]1)=[O:4]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 61147Bromoacetyl bromideHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 636798462-Bromo-1-(4-pyrimidin-2-ylpiperazin-1-yl)ethanoneYield 0.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

20.2 g bromacetylbromide was dropped to 16.5 g 1-pyrimidin-2-yl-piperazin and 10.2 g triethylamine in 250 mL THF. The reaction was stirred over night at RT and evaporated. The residue was extracted with DCM and water. The organic layer was evaporated and the residue was crystallized with petrolether and then purified by chromatography on silica gel (DCM/MeOH:95/5) to yield 36 mg of the desired compound.

Workup

  1. customevaporated
  2. extractionThe residue was extracted with DCM and water
  3. customThe organic layer was evaporated
  4. customthe residue was crystallized with petrolether
  5. custompurified by chromatography on silica gel (DCM/MeOH:95/5)

Sources & evidence

ORD record
ord-f971d6ac5dfa4b12a4f4c5f44ffe44c2
Source dataset
uspto-grants-2014_09
Patent number
US08822464B2

Linked notes

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