Sodium hydride → 2-Bromo-5-(4-methylpiperazin-1-YL)pyrazine

HRID 1157310Notes

Reaction equation

HRID 1157310 reaction equation
[H-].[Na+].[CH3:3][N:4]1[CH2:9][CH2:8][NH:7][CH2:6][CH2:5]1.Br[C:11]1[C:16]([Br:17])=[N:15][CH:14]=[CH:13][N:12]=1>C1COCC1>[Br:17][C:16]1[CH:11]=[N:12][C:13]([N:7]2[CH2:8][CH2:9][N:4]([CH3:3])[CH2:5][CH2:6]2)=[CH:14][N:15]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 531671-MethylpiperazineHCID 138675722,3-Dibromopyrazine

Product 1

HCID 457877252-Bromo-5-(4-methylpiperazin-1-YL)pyrazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To sodium hydride (0.20 g) taken in dry THF (15 ml), N-methyl piperazine (0.93 ml) was added under nitrogen at 0° C. 2,3-Dibromopyrazine (2 g) taken in 15 ml dry THF was added to the above mixture at 0° C. The reaction mixture was allowed to reflux for overnight and quenched with water (5 ml). The organic layer was removed under vacuum. The resulting crude mass was purified by column chromatography to afford 2-bromo-5-(4-methylpiperazin-1-yl)pyrazine as pure product.

Workup

  1. additionwas added to the above mixture at 0° C
  2. temperatureto reflux for overnight
  3. customquenched with water (5 ml)
  4. customThe organic layer was removed under vacuum
  5. customThe resulting crude mass was purified by column chromatography

Sources & evidence

ORD record
ord-19fe532ae53b45c6ae9611834c4732c5
Source dataset
uspto-grants-2010_10
Patent number
US07807671B2

Reaction notes

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