Water → 2-[4-(5-Bromopyrimidin-2-yl)piperazin-1-yl]ethanol

HRID 2068687Notes

Reaction equation

HRID 2068687 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][CH:7]=1.C([O-])([O-])=O.[K+].[K+].Br[CH2:21][CH2:22][OH:23].O>CC(C)=O>[Br:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH2:21][CH2:22][OH:23])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 108982-BromoethanolHCID 11430Potassium CarbonateHCID 27571751-(5-Bromopyrimidin-2-yl)piperazine

Product 1

HCID 27610372-[4-(5-Bromopyrimidin-2-yl)piperazin-1-yl]ethanolYield 47%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 5-bromo-2-(piperazin-1-yl)pyrimidine (0.20 g, 0.83 mmol) in acetone (10.0 mL) was added K2CO3 (0.58 g, 4.17 mmol) followed by the addition of 2-bromoethanol (0.01 g, 1.66 mmol). The resulting reaction mixture was heated to reflux for 3 h. After the completion of reaction (TLC monitoring), the reaction mixture was cooled, added water and extracted with EtOAc (2×100 mL). The combined organics was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified over silica gel (100-200 M, 2% MeOH-DCM) to obtain the desired product (0.11 g, 47%). MS: 287.10 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas heated
  3. temperatureto reflux for 3 h
  4. customAfter the completion of reaction (TLC monitoring)
  5. temperaturethe reaction mixture was cooled
  6. extractionextracted with EtOAc (2×100 mL)
  7. washThe combined organics was washed with brine
  8. dry with materialdried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customThe crude residue was purified over silica gel (100-200 M, 2% MeOH-DCM)

Sources & evidence

ORD record
ord-a44aee34b83146059c61ecf224e6bc30
Source dataset
uspto-grants-2012_10
Patent number
US08299065B2

Reaction notes

Loading…