Sodium Hydroxide → 3-(4-Isopropyl-1-piperazinyl)-2(1H)-pyrazinone

HRID 1295715Notes

Reaction equation

HRID 1295715 reaction equation
[OH-:1].[Na+].Cl[C:4]1[C:9]([N:10]2[CH2:15][CH2:14][N:13]([CH:16]([CH3:18])[CH3:17])[CH2:12][CH2:11]2)=[N:8][CH:7]=[CH:6][N:5]=1>O.CS(C)=O>[CH:16]([N:13]1[CH2:14][CH2:15][N:10]([C:9]2[C:4](=[O:1])[NH:5][CH:6]=[CH:7][N:8]=2)[CH2:11][CH2:12]1)([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 616994222-Chloro-3-(4-isopropylpiperazin-1-yl)pyrazine

Product 1

HCID 693643353-(4-Isopropyl-1-piperazinyl)-2(1H)-pyrazinone

Reagents, catalysts & solvents 1

HCID 23503278(Methanesulfinyl)methane--water (1/1)Solvent

Conditions

Temperature
80 °C

Procedure

To a solution of NaOH (5.4 g, 125 mmol) in a mixture of water/DMSO (1: 1; 15 mL) was added 2-chloro-3-(4-isopropylpiperazin-1-yl)pyrazine (2.66 g, 12 mmol; from Step 1). After being stirred at 80° C. for 2 h, the dark red solution was cooled to room temperature, extracted with EtOAc overnight to give, after drying and solvent removal in vacuo, 2.6 g (70%) of the title compound as a white solid. HPLC purity: 87%. MS m/z 223 (M+H)+. HRMS m/z calcd for C11H18N4O (M)+ 222.1481, found 222.1489.

Workup

  1. temperaturethe dark red solution was cooled to room temperature
  2. extractionextracted with EtOAc overnight
  3. customto give
  4. customafter drying
  5. customsolvent removal in vacuo, 2.6 g (70%) of the title compound as a white solid

Sources & evidence

ORD record
ord-15f3c63187494e299bc338f8a16ae406
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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