5-Octyloxy-2-(3-fluorophenyl)pyrimidine → 5-Octyloxy-2-[4-(3-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy)-3-fluorophenyl]pyrimidine
Reaction equation
[CH2:1]([O:9][C:10]1[CH:11]=[N:12][C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[N:14][CH:15]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].C(OC1C=NC(C2C=CC([O:42][CH2:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([O:51][C:52]([F:62])([F:61])[C:53]([F:60])([F:59])[O:54][C:55]([F:58])([F:57])[F:56])([F:50])[F:49])=CC=2)=NC=1)CCCCC>>[CH2:1]([O:9][C:10]1[CH:15]=[N:14][C:13]([C:16]2[CH:21]=[CH:20][C:19]([O:42][CH2:43][CH2:44][CH2:45][O:46][CH2:47][C:48]([O:51][C:52]([F:61])([F:62])[C:53]([F:59])([F:60])[O:54][C:55]([F:57])([F:58])[F:56])([F:50])[F:49])=[C:18]([F:22])[CH:17]=2)=[N:12][CH:11]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared essentially as in Example 1 by combining 5-octyloxy-2-(3-fluorophenyl)pyrimidine (2.0 g, 6.3 mmol) with 3-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)propoxy chloride (2.5 g, 7.0 mmol, Example 17). The reaction mixture was quenched with water, and the resulting crude product was further purified by recrystallization from ethanol, followed by Kugelrohr distillation (210-18° C. at 0.15 torr), to provide a yield of 3.2 g.
Workup
- customThe reaction mixture was quenched with water
- customthe resulting crude product was further purified by recrystallization from ethanol
- distillationfollowed by Kugelrohr distillation (210-18° C. at 0.15 torr)
- customto provide a yield of 3.2 g
Sources & evidence
- ORD record
- ord-44ca89806ef9475cbc6d8e13c179fe1f
- Source dataset
- uspto-grants-1999_07
- Patent number
- US05928562
Reaction notes
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