HCID 21832552, compound → HCID 53646587, compound
Reaction equation
C(OCC(F)(F)C(F)(F)C(F)([F:12])CO)CCC.[CH2:18]([C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][C@@H:40](O)[CH2:41][O:42][CH2:43][C:44]([F:58])([F:57])[C:45]([F:56])([F:55])[C:46]([F:54])([F:53])[CH2:47][O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:34][CH:33]=2)=[N:30][CH:31]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]>>[CH2:18]([C:26]1[CH:27]=[N:28][C:29]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][C@H:40]([F:12])[CH2:41][O:42][CH2:43][C:44]([F:58])([F:57])[C:45]([F:56])([F:55])[C:46]([F:54])([F:53])[CH2:47][O:48][CH2:49][CH2:50][CH2:51][CH3:52])=[CH:34][CH:33]=2)=[N:30][CH:31]=1)[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH3:25]Participants
3
Procedure
The title compound was prepared essentially as described in Examples 3 and 4 by combining 5-butoxy-2,2,3,3,4,4-hexafluoropentanol (3.1 g, 11.7 mmol, prepared essentially by the method described in U.S. Pat. No. 5,399,291 (Janulis et al.)) with (S)-5-octyl-2-[4-(2,3-oxiranylpropoxy)phenyl]pyrimidine (2.0 g, 5.87 mmol) to produce 5-octyl-2-[4-((S)-2-hydroxy-3-(-5-butoxy-2,2,3,3,4,4-hexafluoropentoxy)propoxy)phenyl]pyrimidine. This chiral (S)-hydroxy compound (2.0 g, 3.3 mmol) was treated with diethylaminosulfur trifluoride (1.06 g, 6.6 mmol) to produce the title compound.
Workup
- customprepared essentially by the method
Sources & evidence
- ORD record
- ord-286822d868594872992597aad2f8d453
- Source dataset
- uspto-grants-1999_10
- Patent number
- US05972241
Reaction notes
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