Sodium borohydride → 4'-({2-Ethyl-1-[4-(2-hydroxy-1,1-dimethylethoxy)phenyl]-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrile

HRID 1674217Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1674217
[BH4-].[Na+].[Cl-].[Ca+2].[Cl-].[C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[C:26](=[O:27])[N:25]([C:28]3[CH:42]=[CH:41][C:31]([O:32][C:33]([CH3:40])([CH3:39])[C:34](OCC)=[O:35])=[CH:30][CH:29]=3)[C:24]([CH2:43][CH3:44])=[N:23][C:22]=2[CH2:45][CH2:46][CH3:47])=[CH:16][CH:15]=1)#[N:7]>C(O)C.O1CCCC1.C(OCC)(=O)C.Cl>[CH2:43]([C:24]1[N:25]([C:28]2[CH:29]=[CH:30][C:31]([O:32][C:33]([CH3:40])([CH3:39])[CH2:34][OH:35])=[CH:41][CH:42]=2)[C:26](=[O:27])[C:21]([CH2:20][C:17]2[CH:16]=[CH:15][C:14]([C:9]3[C:8]([C:6]#[N:7])=[CH:13][CH:12]=[CH:11][CH:10]=3)=[CH:19][CH:18]=2)=[C:22]([CH2:45][CH2:46][CH3:47])[N:23]=1)[CH3:44]

Komponenten

8

Edukt 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460859HCID 57460859, Verbindung

Produkt 1

HCID 574608604'-({2-Ethyl-1-[4-(2-hydroxy-1,1-dimethylethoxy)phenyl]-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl}methyl)biphenyl-2-carbonitrileAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 702EthanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of sodium borohydride (0.84 g) in ethanol (20 mL)-tetrahydrofuran (20 mL) was added calcium chloride (1.2 g) under ice-cooling, and the mixture was stirred for 15 min. A solution of ethyl 2-{4-[5-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethyl-6-oxo-4-propylpyrimidin-1(6H)-yl]phenoxy}-2-methylpropanoate (1.6 g) in tetrahydrofuran (20 mL) was added, and the mixture was further stirred for 2 hr. Small pieces of ice were added in the reaction mixture, and the mixture was stirred for 15 min, and diluted with ethyl acetate and 1 M hydrochloric acid. The organic layer was separated, washed with saturated sodium hydrogen carbonate and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound as a colorless solid (1.0 g, 71%).

Aufarbeitung

  1. temperaturecooling
  2. stirringthe mixture was further stirred for 2 hr
  3. additionSmall pieces of ice were added in the reaction mixture
  4. stirringthe mixture was stirred for 15 min
  5. customThe organic layer was separated
  6. washwashed with saturated sodium hydrogen carbonate and saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-388dc3635795476eaeb7fb660bffae92
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US07998968B2

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