3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propyl chloride → 5-Hexyloxy-2-[4-(3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propoxy)phenyl]pyrimidine
Reaction equation
[F:1][C:2]([F:35])([C:31]([F:34])([F:33])[F:32])[C:3]([F:30])([F:29])[C:4]([F:28])([F:27])[O:5][C:6]([F:26])([F:25])[C:7]([F:24])([F:23])[O:8][C:9]([F:22])([F:21])[CH2:10][O:11][CH2:12][C@@H:13]([F:20])[CH2:14][O:15][CH2:16][CH2:17][CH2:18]Cl.[CH2:36]([O:42][C:43]1[CH:44]=[N:45][C:46]([C:49]2[CH:54]=[CH:53][C:52]([OH:55])=[CH:51][CH:50]=2)=[N:47][CH:48]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]>>[CH2:36]([O:42][C:43]1[CH:48]=[N:47][C:46]([C:49]2[CH:50]=[CH:51][C:52]([O:55][CH2:18][CH2:17][CH2:16][O:15][CH2:14][C@H:13]([F:20])[CH2:12][O:11][CH2:10][C:9]([O:8][C:7]([F:24])([F:23])[C:6]([F:26])([F:25])[O:5][C:4]([F:28])([F:27])[C:3]([F:30])([F:29])[C:2]([F:35])([F:1])[C:31]([F:34])([F:33])[F:32])([F:22])[F:21])=[CH:53][CH:54]=2)=[N:45][CH:44]=1)[CH2:37][CH2:38][CH2:39][CH2:40][CH3:41]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared essentially as described in Example 8 of International Patent Publication No. WO 96/33251 by combining 3-(3-(2-(2-(nonafluorobutoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)propyl chloride (3.0 g, 5.1 mmol) with 5-hexyloxy-2-(4-hydroxyphenyl)pyrimidine (1.4 g, 5.1 mmol). The resulting crude product was purified by Kugelrohr distillation (b.p. 170-80° C. at 0.01 torr).
Workup
- distillationThe resulting crude product was purified by Kugelrohr distillation (b.p. 170-80° C. at 0.01 torr)
Sources & evidence
- ORD record
- ord-94dfefbda023429ea30f62a07c8b3602
- Source dataset
- uspto-grants-2000_02
- Patent number
- US06030547
Reaction notes
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