Sodium Iodide → N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amine

HRID 24925

Reaction equation

HRID 24925 reaction equation
Cl.[N+:2]([C:5]1[CH:12]=[CH:11][C:8]([CH2:9][NH2:10])=[CH:7][CH:6]=1)([O-:4])=[O:3].C(=O)([O-])[O-].[Na+].[Na+].[I-].[Na+].Cl[C:22]1[N:27]=[CH:26][CH:25]=[CH:24][N:23]=1>C(O)C>[N:23]1[CH:24]=[CH:25][CH:26]=[N:27][C:22]=1[NH:10][CH2:9][C:8]1[CH:7]=[CH:6][C:5]([N+:2]([O-:4])=[O:3])=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 10340Sodium CarbonateHCID 744042-ChloropyrimidineHCID 112524674-Nitrobenzylamine hydrochloride

Product 1

HCID 22569285N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

9.4 g (50 mmol) of 4-nitrobenzylamine-hydrochloride, 11.7 g (110 mmol) of sodium carbonate and 7.5 g (50 mmol) of sodium iodide are added to a solution of 5.7 g (50 mmol) of 2-chloropyrimidine in 250 ml of ethanol. The mixture is refluxed for 20 hours. Then the salts are removed by suction filtering, the filtrate is evaporated down and taken up in 300 ml of ethyl acetate. It is washed with water, the solvent is eliminated in vacuo and the residue is chromatographed on silica gel (dichloromethane/methanol=97:3).

Workup

  1. temperatureThe mixture is refluxed for 20 hours
  2. customThen the salts are removed by suction
  3. filtrationfiltering
  4. customthe filtrate is evaporated down
  5. washIt is washed with water
  6. customthe residue is chromatographed on silica gel (dichloromethane/methanol=97:3)

Sources & evidence

ORD record
ord-ac39fbc2361146da9b0c5a09401c6fad
Source dataset
uspto-grants-2005_02
Patent number
US06855710B2

Linked notes

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