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

HRID 1295710Notes

Reaction equation

HRID 1295710 reaction equation
[OH-:1].[Na+].Cl[C:4]1[C:5]([N:10]2[CH2:15][CH2:14][N:13]([CH3:16])[CH2:12][CH2:11]2)=[N:6][CH:7]=[CH:8][N:9]=1>O.CS(C)=O>[CH3:16][N:13]1[CH2:14][CH2:15][N:10]([C:5]2[C:4](=[O:1])[NH:9][CH:8]=[CH:7][N:6]=2)[CH2:11][CH2:12]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 220363522-Chloro-3-(4-methylpiperazin-1-YL)pyrazine

Product 1

HCID 693657953-(4-Methyl-1-piperazinyl)-2(1H)-pyrazinone

Reagents, catalysts & solvents 1

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

Procedure

To a solution of NaOH (5.4 g, 125 mmol) in a mixture of water/DMSO (1:1; 15 mL) at 80° C. was added 1-(3-chloro-2-pyrazinyl)-4-methylpiperazine (obtained in Step 1 above; 2.5 g, 12 mmol). After being stirred 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, 0.96 g (43%) of the title compound as an off-white solid. HPLC purity: 88%. MS m/z 195 (M+H)+. HRMS m/z calcd for C9H14N4O (M)+ 194.1168, found 194.1159.

Workup

  1. extractionextracted with EtOAc overnight
  2. customto give
  3. customafter drying
  4. customsolvent removal in vacuo, 0.96 g (43%) of the title compound as an off-white solid

Sources & evidence

ORD record
ord-676a2dc45a7b454d967becb4a4cae845
Source dataset
uspto-grants-2007_07
Patent number
US07244722B2

Reaction notes

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