Triethylamine → 5-Chloro-2,6-dimethyl-4-{2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethylamino}pyrimidine

HRID 231111Notes

Reaction equation

HRID 231111 reaction equation
C(N(CC)CC)C.[CH2:8]([O:10][CH2:11][CH2:12][C:13]1[CH:22]=[CH:21][C:16]([O:17][CH2:18][CH2:19][NH2:20])=[C:15]([CH3:23])[CH:14]=1)[CH3:9].Cl[C:25]1[C:30]([Cl:31])=[C:29]([CH3:32])[N:28]=[C:27]([CH3:33])[N:26]=1>C1(C)C=CC=CC=1>[Cl:31][C:30]1[C:25]([NH:20][CH2:19][CH2:18][O:17][C:16]2[CH:21]=[CH:22][C:13]([CH2:12][CH2:11][O:10][CH2:8][CH3:9])=[CH:14][C:15]=2[CH3:23])=[N:26][C:27]([CH3:33])=[N:28][C:29]=1[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 139099682-[4-(2-Ethoxyethyl)-2-methylphenoxy]ethan-1-amineHCID 156261074,5-Dichloro-2,6-dimethylpyrimidine

Product 1

HCID 139099835-Chloro-2,6-dimethyl-4-{2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethylamino}pyrimidineYield 55.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1.0 g of triethylamine and 2.2 g of 2-[4-(2-ethoxyethyl)-2-methylphenoxy]ethylamine were added to 1.8 g of 4,5-dichloro-2,6-dimethylpyrimidine dissolved in 50 ml of toluene. The mixture was heated under reflux, whilst stirring, for 5 hours. At the end of this time, the reaction product was washed with water and dried over anhydrous sodium sulfate. Toluene was then removed by distillation under reduced pressure, and the oily product obtained was subjected to column chromatography (Wakogel C-200, eluted with a 2:1 by volume mixture of toluene and etyl acetate) to isolate the product. The crystals obtained were recrystallized from hexane, to give 2.0 g of the title compound as colorless granular crystals melting at 61°-63° C.

Workup

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

Sources & evidence

ORD record
ord-a171694621ec4fe1b4585c73f7e67502
Source dataset
uspto-grants-1989_07
Patent number
US04845097

Reaction notes

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