Methylamine → 5-Bromo-N-methylpyrimidin-2-amine

HRID 1876512Notes

Reaction equation

HRID 1876512 reaction equation
[CH3:1][NH2:2].[Br:3][C:4]1[CH:5]=[N:6][C:7](Cl)=[N:8][CH:9]=1>CO>[Br:3][C:4]1[CH:5]=[N:6][C:7]([NH:2][CH3:1])=[N:8][CH:9]=1

Participants

4

Procedure

40% Aqueous methylamine solution (35 ml) and methanol (20 ml) were added to 5-bromo-2-chloropyrimidine (3 μg, 15.5 mmol) and the resulting mixture was heated to reflux for 3 days. The mixture was cooled, then the solvent was evaporated under reduced pressure, the residue was partitioned with methylene chloride and 1 M sodium hydroxide, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (3.0 g, 100%) as a white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 3 days
  3. temperatureThe mixture was cooled
  4. customthe solvent was evaporated under reduced pressure
  5. customthe residue was partitioned with methylene chloride and 1 M sodium hydroxide
  6. dry with materialthe organic layer was dried over magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-7653f04a989846929be02fc0670fa8bf
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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