1,3-Propanediamine → N-(3-aminopropyl)pyrimidin-2-amine

HRID 1603685Notes

Reaction equation

HRID 1603685 reaction equation
Cl[C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8]([NH2:12])[CH2:9][CH2:10][NH2:11]>C1(C)C=CC=CC=1>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[NH:11][CH2:10][CH2:9][CH2:8][NH2:12]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 744042-Chloropyrimidine

Product 1

HCID 14397405N-(3-aminopropyl)pyrimidin-2-amineYield 164.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-chloro-pyrimidine (24.3 g) was added portionwise to a mixture of 1,3-propanediamine (85 g) in toluene (240 mL) while stirring at reflux temperature. The reaction mixture was stirred and refluxed for 3 hours. The reaction mixture was cooled, the precipitate was filtered off and the filtrate was evaporated. The residue was distilled in vacuo, yielding 53 g (65.7%) of N-2-pyrimidinyl-1,3-propanediamine (intermediate 1).

Workup

  1. temperatureat reflux temperature
  2. stirringThe reaction mixture was stirred
  3. temperaturerefluxed for 3 hours
  4. temperatureThe reaction mixture was cooled
  5. filtrationthe precipitate was filtered off
  6. customthe filtrate was evaporated
  7. distillationThe residue was distilled in vacuo

Sources & evidence

ORD record
ord-ee8833959859498db69cc2e1cbad9c0a
Source dataset
uspto-grants-1999_11
Patent number
US05990123

Reaction notes

Loading…