Water → 5-(4-(Butoxy)butoxy)-2-[4-(-3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)phenyl]pyrimidine

HRID 1740688Notes

Reaction equation

O[C:2]1C=CN=[C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]([F:42])[CH2:17][O:18][CH2:19][C:20]([O:23][C:24]([F:41])([F:40])[C:25]([F:39])([F:38])[O:26][C:27]([F:37])([F:36])[C:28]([F:35])([F:34])[O:29][C:30]([F:33])([F:32])[F:31])([F:22])[F:21])=[CH:10][CH:9]=2)[N:3]=1.[CH2:43]([O:47][CH2:48][CH2:49][CH2:50][CH2:51]Cl)[CH2:44][CH2:45][CH3:46].C(=O)([O-])[O-:54].[K+].[K+].O.[C:60](#[N:62])[CH3:61]>CN(C)C=O>[CH2:43]([O:47][CH2:48][CH2:49][CH2:50][CH2:51][O:54][C:61]1[CH:60]=[N:62][C:4]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH2:15][C@@H:16]([F:42])[CH2:17][O:18][CH2:19][C:20]([O:23][C:24]([F:40])([F:41])[C:25]([F:38])([F:39])[O:26][C:27]([F:36])([F:37])[C:28]([F:34])([F:35])[O:29][C:30]([F:32])([F:33])[F:31])([F:21])[F:22])=[CH:10][CH:9]=2)=[N:3][CH:2]=1)[CH2:44][CH2:45][CH3:46]

Participants

Conditions

Temperature: 63 °C

Procedure

The title compound was prepared by combining 5-(4-hydroxy-2-[4-(3-(2-(2-(2-(trifluoromethoxy)tetrafluoroethoxy)tetrafluoroethoxy)-2,2-difluoroethoxy)-(S)-2-fluoropropoxy)phenyl]pyrimidine (2.0 g, prepared essentially as in Example 18), 4-butoxybutyl chloride (0.63 g), and potassium carbonate (0.58 g) in a mixture of acetonitrile (12 mL) and dimethylformamide (16 mL). The resulting mixture was heated to 63° C. for 12 hours. Deionized water (30 mL) was added to the mixture, and the mixture was cooled to 0° C. and filtered to obtain the resulting crude product. The crude product was recrystallized form ethanol and further purified by Kugelrohr distillation (b.p. 196° C. at 0.04 torr; yield 1.71 g).

Workup

temperaturethe mixture was cooled to 0° C.
filtrationfiltered

Sources & evidence

ORD record: ord-1101bf973b1f4e4f8da6014e9ff1cd1c
Source dataset: uspto-grants-1999_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05972241

Reaction notes

Loading…