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

HRID 336359Notes

Reaction equation

HRID 336359 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-df1e764b7f984c31996312bf9931eef1
Source dataset
uspto-grants-2014_11
Patent number
US08889677B2

Reaction notes

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