Triethylamine → N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amine

HRID 1277287Notes

Reaction equation

HRID 1277287 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][NH2:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].Cl[C:13]1[N:18]=[CH:17][CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>C(O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH2:8][NH:9][C:13]2[N:18]=[CH:17][CH:16]=[CH:15][N:14]=2)=[CH:10][CH:11]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 291474-NitrobenzylamineHCID 744042-Chloropyrimidine

Product 1

HCID 22569285N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amineYield 11%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 4-nitrobenzylamine (6.09 g, 40.0 mmol), 2-chloropyrimidine (4.82 g, 42.1 mmol), triethylamine (11.2 ml, 80.4 mmol) and ethanol (120 ml) was stirred at 110° C. for 24 hours, and the mixture was concentrated under reduced pressure. To the residue was added water, and the mixture wasextractedwithethylacetate-THF. Theorganiclayerwas dried with anhydrous sodium sulfate and concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-ethanol to give N-(4-nitrobenzyl)-N-(2-pyrimidinyl)amine (0.99 g, 4.3 mmol, 11%).

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionTo the residue was added water
  3. dry with materialTheorganiclayerwas dried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-a7811ee926474578b8fbab9446a1c149
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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