5-Octyl-2-[4-(4-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)butoxy)phenyl]pyrimidine → 5-Heptyloxy-2-[4-(4-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)butoxy)phenyl]pyrimidine
Reaction equation
C(C1C=NC(C2C=CC(O[CH2:22][CH2:23][CH2:24][CH2:25][O:26][CH2:27][C:28]([O:31][C:32]([F:49])([F:48])[C:33]([F:47])([F:46])[O:34][C:35]([F:45])([F:44])[C:36]([F:43])([F:42])[O:37][C:38]([F:41])([F:40])[F:39])([F:30])[F:29])=CC=2)=NC=1)CCCCCCC.[CH2:50]([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)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]>>[CH2:50]([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][CH2:25][O:26][CH2:27][C:28]([O:31][C:32]([F:48])([F:49])[C:33]([F:46])([F:47])[O:34][C:35]([F:44])([F:45])[C:36]([F:42])([F:43])[O:37][C:38]([F:40])([F:41])[F:39])([F:30])[F:29])=[CH:68][CH:69]=2)=[N:60][CH:59]=1)[CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared essentially as in Example 1 by combining 4-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy) 1-bromobutane (6.1 g, 15.0 mmol, Example 25) with 5-heptyloxy-2-(4-hydroxyphenyl)pyrimidine (3 g, 10.5 mmol). The resulting crude product was further purified by recrysallization from ethanol and subsequent Kugelrohr distillation (b.p. 200°-210° C. at 0.3 torr; yield of 5.2 g).
Workup
- distillationThe resulting crude product was further purified by recrysallization from ethanol and subsequent Kugelrohr distillation (b.p. 200°-210° C. at 0.3 torr; yield of 5.2 g)
Sources & evidence
- ORD record
- ord-29917576a2d1494cbf612f1b25e8903d
- Source dataset
- uspto-grants-1997_08
- Patent number
- US05658491
Reaction notes
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