Acetonitrile → 5-Hexyloxy-2-[4-(5-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

HRID 341708Notes

Reaction equation

HRID 341708 reaction equation
[F:1][C:2]([F:32])([C:28]([F:31])([F:30])[F:29])[C:3]([F:27])([F:26])[C:4]([F:25])([F:24])[O:5][C:6]([F:23])([F:22])[C:7]([F:21])([F:20])[O:8][C:9]([F:19])([F:18])[CH2:10][O:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]Br.[CH2:33]([O:39][C:40]1[CH:41]=[N:42][C:43]([C:46]2[CH:51]=[CH:50][C:49]([OH:52])=[CH:48][CH:47]=2)=[N:44][CH:45]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+].C(#N)C>O.C1(C)C=CC=CC=1>[CH2:33]([O:39][C:40]1[CH:45]=[N:44][C:43]([C:46]2[CH:47]=[CH:48][C:49]([O:52][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][O:11][CH2:10][C:9]([O:8][C:7]([F:21])([F:20])[C:6]([F:23])([F:22])[O:5][C:4]([F:25])([F:24])[C:3]([F:27])([F:26])[C:2]([F:32])([F:1])[C:28]([F:31])([F:30])[F:29])([F:19])[F:18])=[CH:50][CH:51]=2)=[N:42][CH:41]=1)[CH2:34][CH2:35][CH2:36][CH2:37][CH3:38]

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 212253085-(2-(2-(Nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-bromopentaneHCID 1361744305-Hexyloxy-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 212253455-Hexyloxy-2-[4-(5-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)pentyloxy)phenyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

A 500 mL flask was charged with 5-(2-(2 -(nonafluorobutoxy)tetrafluoroethoxy)-2,2 -difluoroethoxy)-l-bromopentane (18.6 g, 32 mmol; prepared from 1,5-dibromopentane and 2-(2 -(nonafluorobutoxy)tetrafluoroethoxy)-2,2 -difluoroethanol), 5-hexyloxy-2-(4 -hydroxyphenyl)pyrimidine (8.0 g, 29.4 mmol), potassium carbonate (5.4 g, 39 mmol), and acetonitrile (200 mL), and the resulting mixture was stirred and refluxed overnight under nitrogen. Toluene (150 mL) and water (150 mL) were added to the refluxed mixture. The resulting toluene layer was collected and residual water removed by distillation using a Dean-Stark apparatus. The toluene layer was then filtered through a pad of silica gel and the toluene removed under reduced pressure. The crude product was further purified by distillation using a Kugelrohr apparatus (b.p. 210°- 25° C. at 0.3 torr)

Workup

  1. temperaturerefluxed overnight under nitrogen
  2. customThe resulting toluene layer was collected
  3. customresidual water removed by distillation
  4. filtrationThe toluene layer was then filtered through a pad of silica gel
  5. customthe toluene removed under reduced pressure
  6. distillationThe crude product was further purified by distillation

Sources & evidence

ORD record
ord-7aaaae84e7c14c7d80b48ffdd107cef4
Source dataset
uspto-grants-1999_01
Patent number
US05855812

Reaction notes

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