Methylamine → 5-Bromo-2-(methylaminocarbonylmethyl)aminopyridine

HRID 18252Notes

Reaction equation

HRID 18252 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]([O:14]C)=O)=[N:8][CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[CH:6][C:7]([NH:10][CH2:11][C:12]([NH:2][CH3:1])=[O:14])=[N:8][CH:9]=1

Participants

4

Reactant 2

HCID 6329MethylamineHCID 22139049Methyl 2-((5-bromopyridin-2-yl)amino)acetate

Product 1

HCID 221390975-Bromo-2-(methylaminocarbonylmethyl)aminopyridineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2.0 M methylamine in MeOH (75 mL) was added to 5-bromo-2-(methoxycarbonylmethyl)aminopyridine (2.9 g, 12 mmole). The reaction was stirred for 24 h then was concentrated to dryness. The residue was triturated with 10% petroleum ether/Et2O (100 mL), then was collected and dried under vacuum to give the title compound (2.96 g, 100%) as an off-white solid: MS (ES) m/e 244.2 (M+H)+.

Workup

  1. concentrationthen was concentrated to dryness
  2. customThe residue was triturated with 10% petroleum ether/Et2O (100 mL)
  3. customwas collected
  4. customdried under vacuum

Sources & evidence

ORD record
ord-4d3a2aae5211431d955fbb3972f129b0
Source dataset
uspto-grants-2010_06
Patent number
US07741339B2

Reaction notes

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