Triethylamine → 6-Chloro-N4-[(2-fluorophenyl)methyl]-2,4-pyrimidinediamine

HRID 1590632Notes

Reaction equation

HRID 1590632 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([Cl:9])[N:3]=1.[F:10][C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[CH2:13][NH2:14].C(N(CC)CC)C>C(O)C>[NH2:1][C:2]1[N:3]=[C:4]([Cl:9])[CH:5]=[C:6]([NH:14][CH2:13][C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=2[F:10])[N:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 655222-Amino-4,6-dichloropyrimidineHCID 666492-Fluorobenzylamine

Product 1

HCID 197677166-Chloro-N4-[(2-fluorophenyl)methyl]-2,4-pyrimidinediamine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

53 g (323 mmol) of 2-amino-4,6-dichloropyrimidine, 40.4 g (323 mmol) of 2-fluorobenzylamine and 33.4 g (330 mmol) of triethylamine are dissolved in 800 ml of ethanol and the reaction mixture is heated under reflux for 20 hours. After 400 ml of ethanol have been distilled off, the residue is diluted with 500 ml of water, and the precipitated product is filtered off with suction and recrystallised from 1 l of toluene. In this manner 2-amino-4-chloro-6-(2-fluorobenzylamino)-pyrimidine having a melting point of 130°-133° is obtained.

Workup

  1. temperaturethe reaction mixture is heated
  2. temperatureunder reflux for 20 hours
  3. distillationAfter 400 ml of ethanol have been distilled off
  4. additionthe residue is diluted with 500 ml of water
  5. filtrationthe precipitated product is filtered off with suction
  6. customrecrystallised from 1 l of toluene

Sources & evidence

ORD record
ord-13af4c08ccc846eb92316557543ffea5
Source dataset
uspto-grants-1993_04
Patent number
US05204353

Reaction notes

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