Water → 5-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamine

HRID 1045767Notes

Reaction equation

HRID 1045767 reaction equation
[Br:1][C:2]1[C:3]([NH2:18])=[C:4]([N+:15]([O-])=O)[C:5]([N:8]2[CH2:13][CH2:12][N:11]([CH3:14])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[O-]S(S([O-])=O)=O.[Na+].[Na+].O>C(O)C>[Br:1][C:2]1[C:3]([NH2:18])=[C:4]([NH2:15])[C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH3:14])[CH2:12][CH2:13]2)=[N:6][CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 58446993HCID 58446993, compound

Product 1

HCID 584469905-Bromo-2-(4-methyl-1-piperazinyl)-3,4-pyridinediamineYield 81.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250 mL round bottom flask was charged with 5-bromo-2-(4-methylpiperazin-1-yl)-3-nitropyridin-4-amine (1.5 g, 4.7 mmol), Na2S2O4 (2.0 g, 11 mmol), water (10 mL) and ethanol (20 mL). The mixture was heated at reflux for 0.5 h. Work-up: the solvent was evaporated. The residue was re-suspended in triethylamine (15 mL) and ethyl acetate (300 mL), and then filtered. The filtrate was concentrated in vacuo, to afford 1.1 g (80%) of the product as a pale-red solid. MS m/z: 286 (M+H+).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 0.5 h
  3. customthe solvent was evaporated
  4. filtrationethyl acetate (300 mL), and then filtered
  5. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-76cf6eb2822647e9a3e4809ca7aa854f
Source dataset
uspto-grants-2013_10
Patent number
US08569300B2

Reaction notes

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