1,3-Dibromopropane → 5-Octyl-2-[4-(3-(2-(2-(pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 2257467Notes

Reaction equation

HRID 2257467 reaction equation
[CH2:1]([C:9]1[CH:10]=[N:11][C:12]([C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[N:13][CH:14]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[F:22][C:23]([F:45])([O:28][C:29]([F:44])([F:43])[C:30]([F:42])([F:41])[O:31][C:32]([F:40])([F:39])[CH2:33][O:34][CH2:35][CH2:36][CH2:37]Br)[C:24]([F:27])([F:26])[F:25].BrCCCBr.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH2:1]([C:9]1[CH:14]=[N:13][C:12]([C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:37][CH2:36][CH2:35][O:34][CH2:33][C:32]([O:31][C:30]([F:41])([F:42])[C:29]([F:43])([F:44])[O:28][C:23]([F:22])([F:45])[C:24]([F:26])([F:27])[F:25])([F:40])[F:39])=[CH:17][CH:16]=2)=[N:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 80011,3-DibromopropaneHCID 11430Potassium CarbonateHCID 6040552-(4-Hydroxyphenyl)-5-octylpyrimidineHCID 212253073-(2-(2-(Pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propyl bromide

Product 1

HCID 212253065-Octyl-2-[4-(3-(2-(2-(pentafluoroethoxy) tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

The title compound was prepared essentially as in Example 1 by combining 5-octyl-2-(4-hydroxyphenyl)pyrimidine (2.0 g, 7.3 mmol), 3-(2-(2-(pentafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopropane (3.38 g, 7.47 mmol; prepared by combining 1,3-dibromopropane with 3-(2-(2-(pentafluoroethoxy)tetrafluorooethoxy)-2,2-difluoroethanol), and potassium carbonate (1.16 g, 8.43 mmol) in acetonitrile (20 mL) and refluxing the resulting mixture under nitrogen overnight. The mixture was cooled and filtered, and the resulting solids were washed with toluene (50 mL). The toluene was then removed under reduced pressure, and the resulting waxy solid was dissolved in toluene (50 mL) and washed with three 30 mL aliquots of perfluorohexane. After removing the toluene under reduced pressure, the resulting crude product was further purified by silica gel chromatography, eluting with 20 volume percent ethyl acetate/hexane, to yield 3.60 g of purified product.

Workup

  1. customprepared
  2. temperaturerefluxing the resulting mixture under nitrogen overnight
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe resulting solids were washed with toluene (50 mL)
  6. customThe toluene was then removed under reduced pressure
  7. dissolutionthe resulting waxy solid was dissolved in toluene (50 mL)
  8. washwashed with three 30 mL aliquots of perfluorohexane
  9. customAfter removing the toluene under reduced pressure
  10. customthe resulting crude product was further purified by silica gel chromatography
  11. washeluting with 20 volume percent ethyl acetate/hexane

Sources & evidence

ORD record
ord-f95735e29ced44ea9c18998270679eee
Source dataset
uspto-grants-1997_08
Patent number
US05658491

Reaction notes

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