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

HRID 566113Notes

Reaction equation

HRID 566113 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 was extracted with ethyl acetate-THF. The organic layer was 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. extractionthe mixture was extracted with ethyl acetate-THF
  4. dry with materialThe organic layer was dried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-ethanol

Sources & evidence

ORD record
ord-7dba33416d7f4f3387a0bad7417f92c2
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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