Water → 2-[(4,4-difluorocyclohexyl)oxy]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 570698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570698
[H-].[Na+].[F:3][C:4]1([F:11])[CH2:9][CH2:8][CH:7]([OH:10])[CH2:6][CH2:5]1.C(S[C:16]1[N:17]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[CH:30][CH:29]=2)[C:18](=[O:27])[C:19]2[CH:25]=[CH:24][C:23](=[O:26])[NH:22][C:20]=2[N:21]=1)CC.O>O1CCCC1>[F:3][C:4]1([F:11])[CH2:9][CH2:8][CH:7]([O:10][C:16]2[N:17]([C:28]3[CH:29]=[CH:30][C:31]([O:34][CH2:35][C:36]([F:39])([F:38])[F:37])=[CH:32][CH:33]=3)[C:18](=[O:27])[C:19]3[CH:25]=[CH:24][C:23](=[O:26])[NH:22][C:20]=3[N:21]=2)[CH2:6][CH2:5]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 5463004,4-Difluorocyclohexan-1-olHCID 866853582-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Produkt 1

HCID 866853612-[(4,4-difluorocyclohexyl)oxy]-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneAusbeute 39,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of sodium hydride (60% in oil, 19 mg) in tetrahydrofuran (5 ml) was added 4,4-difluorocyclohexanol (109 mg) at room temperature, and the mixture was stirred at room temperature for 10 min. To the reaction mixture was added 2-(propylsulfanyl)-3-[4-(2,2,2-trifluoroethoxy)phenyl]pyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (165 mg), and the mixture was stirred at room temperature for 5 hr. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane), and recrystallized from a mixed solvent of hexane/ethyl acetate to give the title compound (75 mg).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 5 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)
  7. customrecrystallized from a mixed solvent of hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c4fae2e23e474d01a37369442636685e
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023858B2

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