Methylamine → 5-Bromo-3-[(methylamino)methyl]pyridin-2-amine

HRID 225860Notes

Reaction equation

HRID 225860 reaction equation
Br.[NH2:2][C:3]1[C:8]([CH2:9]Br)=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1.[CH3:12][NH2:13]>C1COCC1>[NH2:2][C:3]1[C:8]([CH2:9][NH:13][CH3:12])=[CH:7][C:6]([Br:11])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 221390775-Bromo-3-[(methylamino)methyl]pyridin-2-amineYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the 2-amino-3-(bromomethyl)-5-bromopyridine hydrobromide salt (prepared above) in 40% aqueous methylamine (50 mL) and THF (50 mL) was stirred at RT overnight in a pressure bottle. The reaction solution was concentrated and extracted with EtOAc (2×100 mL). The combined organic phases were washed with H2O, dried over Na2SO4 and concentrated. Purification on silica gel afforded the title compound (4.25 g, 80%) as a yellow oil: MS (ES) m/e 217 (M+H)+.

Workup

  1. concentrationThe reaction solution was concentrated
  2. extractionextracted with EtOAc (2×100 mL)
  3. washThe combined organic phases were washed with H2O
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customPurification on silica gel

Sources & evidence

ORD record
ord-f86ce50d0cc8414db0a5a03f9e3d1201
Source dataset
uspto-grants-2009_07
Patent number
US07557125B2

Reaction notes

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