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

HRID 1428934Notes

Reaction equation

HRID 1428934 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 31.2%

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 mixture was stirred overnight 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 8.9 g 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-b4599b616dfb4990b055fba283194bfe
Source dataset
uspto-grants-2015_01
Patent number
US08937176B2

Reaction notes

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