Piperazine → (R)-1-(4-Piperazin-1-yl-pyrimidin-2-yl)-ethyl acetate

HRID 586198Notes

Reaction equation

HRID 586198 reaction equation
[C:1]([O:4][C@@H:5]([C:7]1[N:12]=[C:11](OS(C)(=O)=O)[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2].[NH:18]1[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]1>O1CCCC1>[C:1]([O:4][C@@H:5]([C:7]1[N:12]=[C:11]([N:18]2[CH2:23][CH2:22][NH:21][CH2:20][CH2:19]2)[CH:10]=[CH:9][N:8]=1)[CH3:6])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 4837PiperazineHCID 54125954(R)-1-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl acetate

Product 1

HCID 10922950(R)-1-(4-Piperazin-1-yl-pyrimidin-2-yl)-ethyl acetateYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (R)-1-(4-methanesulfonyloxy-pyrimidin-2-yl)-ethyl acetate (prepared according to the method of Preparation Six, 24.1 g, 92 mmol) and piperazine (16.0 g, 184 mmol) in tetrahydrofuran (200 mL) was heated at reflux for 1 h. This mixture was cooled, filtered, concentrated, and purified by flash column chromatography (9:1 dichloromethane/methanol) to give 24.4 g (88%) of the title compound as an oil. 1H NMR (CDCl3, 300 MHz) δ 1.56 (d, 3H), 2.25 (s, 3H), 2.83 (m, 4H), 3.63 (m, 4H), 5.54 (q, 1H), 6.38 (d, 1H), 8.24 (d, 1H); MS (CI) 251 (MH+).

Workup

  1. customprepared
  2. temperaturewas heated
  3. temperatureat reflux for 1 h
  4. temperatureThis mixture was cooled
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by flash column chromatography (9:1 dichloromethane/methanol)

Sources & evidence

ORD record
ord-6b025ade4bcb42e39fb12dd0c8eee653
Source dataset
uspto-grants-2005_08
Patent number
US06936600B2

Reaction notes

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