5-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine → 5-Octyloxy-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

HRID 582980Notes

Reaction equation

HRID 582980 reaction equation
C(C1C=NC(C2C=CC(O[CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([O:30][C:31]([F:48])([F:47])[C:32]([F:46])([F:45])[O:33][C:34]([F:44])([F:43])[C:35]([F:42])([F:41])[O:36][C:37]([F:40])([F:39])[F:38])([F:29])[F:28])=CC=2)=NC=1)CCCCCCC.[CH2:49]([O:57][C:58]1[CH:59]=[N:60][C:61]([C:64]2[CH:69]=[CH:68][C:67]([OH:70])=[CH:66][CH:65]=2)=[N:62][CH:63]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]>CN(C)C=O>[CH2:49]([O:57][C:58]1[CH:63]=[N:62][C:61]([C:64]2[CH:65]=[CH:66][C:67]([O:70][CH2:22][CH2:23][CH2:24][O:25][CH2:26][C:27]([O:30][C:31]([F:47])([F:48])[C:32]([F:45])([F:46])[O:33][C:34]([F:43])([F:44])[C:35]([F:41])([F:42])[O:36][C:37]([F:40])([F:39])[F:38])([F:29])[F:28])=[CH:68][CH:69]=2)=[N:60][CH:59]=1)[CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]

Participants

4

Reactant 2

HCID 212253045-Octyl-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidineHCID 135708811Phenol, 4-[5-(octyloxy)-2-pyrimidinyl]-

Product 1

HCID 212252865-Octyloxy-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)phenyl]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

The title compound was prepared essentially as in Example 1 by combining 3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-1-chloropropane (5.2 g, 10.9 mmol, Example 24) with 5-octyloxy-2-(4-hydroxyphenyl)pyrimidine (3 g, 10.0 mmol) in dimethylformamide and stirring at 120° C. overnight. The resulting product was further purified by Kugelrohr distillation (b.p. 195-210° C. at 0.3 torr), followed by recrystallization from ethanol and additional distillation (yield of 3.5 g).

Workup

  1. distillationThe resulting product was further purified by Kugelrohr distillation (b.p. 195-210° C. at 0.3 torr)
  2. customfollowed by recrystallization from ethanol and additional distillation (yield of 3.5 g)

Sources & evidence

ORD record
ord-93dfcce0311747ac8d58e6cda8fcd803
Source dataset
uspto-grants-1999_07
Patent number
US05928562

Reaction notes

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