Cyclopropylamine → HCID 20359978, compound

HRID 2082636Notes

Reaction equation

HRID 2082636 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[C:4](Cl)[N:3]=1.[CH:10]1([NH2:13])[CH2:12][CH2:11]1>C(#N)C>[CH:10]1([NH:13][C:2]2[N:3]=[C:4]([NH:13][CH:10]3[CH2:12][CH2:11]3)[CH:5]=[C:6]([Cl:8])[N:7]=2)[CH2:12][CH2:11]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 773782,4,6-Trichloropyrimidine

Product 1

HCID 20359978HCID 20359978, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 151.5 g (1 mol) of 2,4,6-trichloropyrimidine in 300 ml of acetonitrile is taken and 285 g (5 mols) of cyclopropylamine are added dropwise at 20°-30°, whilst cooling. The solution is warmed to 40° for 5 hours and to 70° for about 12 hours. The suspension is concentrated to dryness on a rotary evaporator and the residue is thoroughly stirred with 1,500 ml of methylene chloride and 1,000 ml of water for 30 minutes. The undissolved constituent is filtered off on a cloth filter. It consists of practically pure 4,6-di-cyclopropylamino-2-chloropyrimidine. The phases of the filtrate are separated and the organic phase is again extracted with water, dried and concentrated to give an oil. This is distilled under a high vacuum (boiling point 149°-51°/0.1 mm) and is then recrystallised from methanol, with addition of water. The colourless product has a melting point of 58°-60°.

Workup

  1. temperaturewhilst cooling
  2. temperatureThe solution is warmed to 40° for 5 hours and to 70° for about 12 hours
  3. concentrationThe suspension is concentrated to dryness on a rotary evaporator
  4. filtrationThe undissolved constituent is filtered off on a cloth
  5. filtrationfilter
  6. customThe phases of the filtrate are separated
  7. extractionthe organic phase is again extracted with water
  8. customdried
  9. concentrationconcentrated
  10. customto give an oil
  11. distillationThis is distilled under a high vacuum (boiling point 149°-51°/0.1 mm)
  12. customis then recrystallised from methanol, with addition of water

Sources & evidence

ORD record
ord-792e6bd9e6fd4a599dbb998ed6898f6a
Source dataset
uspto-grants-1978_04
Patent number
US04082535

Reaction notes

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