Triethylamine → HCID 13909969, compound

HRID 231109Notes

Reaction equation

HRID 231109 reaction equation
Cl[C:2]1[C:7]([Cl:8])=[C:6]([CH3:9])[N:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[CH2:17]([O:19][CH2:20][CH2:21][C:22]1[CH:31]=[CH:30][C:25]([O:26][CH2:27][CH2:28][NH2:29])=[C:24]([CH3:32])[CH:23]=1)[CH3:18]>C1(C)C=CC=CC=1>[Cl:8][C:7]1[C:2]([NH:29][CH2:28][CH2:27][O:26][C:25]2[CH:30]=[CH:31][C:22]([CH2:21][CH2:20][O:19][CH2:17][CH3:18])=[CH:23][C:24]=2[CH3:32])=[N:3][CH:4]=[N:5][C:6]=1[CH3:9]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 117895374,5-Dichloro-6-methylpyrimidineHCID 139099682-[4-(2-Ethoxyethyl)-2-methylphenoxy]ethan-1-amine

Product 1

HCID 13909969HCID 13909969, compoundYield 75.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.6 g of 4,5-dichloro-6-methylpyrimidine was dissolved in 50 ml of toluene. 1.0 g of triethylamine and 2.2 g of 2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethylamine were added to the solution, and the reaction mixture was heated under reflux for 5 hours, whilst stirring. At the end of this time, the reaction mixture was washed with water and dried over anhydrous sodium sulfate. The toluene was removed by distillation under reduced pressure, and the oily product thus obtained was subjected to column chromatography (Wakogel C-200, eluted with a 2:1 by volume mixture of toluene and ethyl acetate) to isolate the product. The crystals thus obtained were recrystallized from hexane to afford 2.6 g of the title compound as colorless needles melting at 57°-58° C.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureunder reflux for 5 hours
  3. washAt the end of this time, the reaction mixture was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe toluene was removed by distillation under reduced pressure
  6. customthe oily product thus obtained
  7. washeluted with a 2:1 by volume mixture of toluene and ethyl acetate)
  8. customto isolate the product
  9. customThe crystals thus obtained
  10. customwere recrystallized from hexane

Sources & evidence

ORD record
ord-d5080429a674458f80aad22769907d15
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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