2-Methoxyethylamine → 2-Amino-5-bromo-3-[(2-methoxyethyl)aminomethyl]pyridine

HRID 18307Notes

Reaction equation

HRID 18307 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].Br.[NH2:7][C:8]1[C:13]([CH2:14]Br)=[CH:12][C:11]([Br:16])=[CH:10][N:9]=1.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:7][C:8]1[C:13]([CH2:14][NH:5][CH2:4][CH2:3][O:2][CH3:1])=[CH:12][C:11]([Br:16])=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 534200525-Bromo-3-(bromomethyl)pyridin-2-amine hydrobromide

Product 1

HCID 221390612-Amino-5-bromo-3-[(2-methoxyethyl)aminomethyl]pyridineYield 90%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methoxyethylamine (1.49 mL, 17.16 mmole) was added to a solution of 2-amino-5-bromo-3-(bromomethyl)pyridine hydrobromide (1.49 g, 4.29 mmole) and DIEA (2.24 mL, 12.87 mmole) in CH2Cl2 (10 mL) at RT. The reaction was stirred overnight then was concentrated in vacuo. The residue was diluted with water and the solution was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over Na2SO4, and concentrated to afford the title compound (1.00 g, 90%) as a light brown liquid after drying in vacuo: MS (ES) m/e 260/262 (M+H)+.

Workup

  1. concentrationthen was concentrated in vacuo
  2. additionThe residue was diluted with water
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe combined organic extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c0f5acefd2d04046a1c5c95838958347
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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