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

HRID 2227844Notes

Reaction equation

HRID 2227844 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) δ1.56 (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-b9f7f1921bbb48e98a81873f448550ac
Source dataset
uspto-grants-2002_07
Patent number
US06414149B1

Reaction notes

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