Isopropylamine → 2,6-Dichloro-N-(propan-2-yl)pyrimidin-4-amine

HRID 2398539Notes

Reaction equation

HRID 2398539 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[CH:10]([NH2:13])([CH3:12])[CH3:11]>>[CH:10]([NH:13][C:6]1[CH:5]=[C:4]([Cl:9])[N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:12])[CH3:11]

Participants

3

Reactant 2

HCID 6363IsopropylamineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 214332662,6-Dichloro-N-(propan-2-yl)pyrimidin-4-amine

Procedure

400 (2.18 mols) of 2,4,6-trichloro-pyrimidine are dissolved in 2000 cc of alcohol. 280 g (4.75 mols) of isopropyl amine in 200 cc of alcohol are added to the solution while stirring and cooling, the temperature being maintained below 30°. The mixture is subsequently stirred at room temperature for a further 60 minutes and the alcohol is then removed by evaporation in a water jet vacuum until the mixture hardens to a solid mass. The solid residue is washed with water and subjected to steam distillation. This distillation is continued until only traces of the steam-volatile 2-isopropylamino-4,6-dichloro-pyrimidine are deposited in the receiver. The steam-nonvolatile 4-isopropylamino-2,6-dichloro-pyrimidine is obtained. After distillation in a vacuum (B.P. 124°/0.1 mm of Hg) the pure product, having a M.P. of 69°-70° after recrystallization from water/alcohol, is obtained.

Workup

  1. temperaturecooling
  2. temperaturethe temperature being maintained below 30°
  3. stirringThe mixture is subsequently stirred at room temperature for a further 60 minutes
  4. customthe alcohol is then removed by evaporation in a water jet vacuum until the mixture
  5. washThe solid residue is washed with water
  6. distillationsubjected to steam distillation
  7. distillationThis distillation

Sources & evidence

ORD record
ord-0e80699bc6534724bbda1b4e2de68d9c
Source dataset
uspto-grants-1977_05
Patent number
US04025515

Reaction notes

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