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

HRID 1718907Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1718907
[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:43]=[CH:42][C:31]([O:32][C:33]4([C:38](OC)=[O:39])[CH2:37][CH2:36][CH2:35][CH2:34]4)=[CH:30][CH:29]=3)[C:24]([CH2:44][CH3:45])=[N:23][C:22]=2[CH2:46][CH2:47][CH3:48])=[CH:16][CH:15]=1)#[N:7]>CO.O1CCCC1.C(OCC)(=O)C.Cl>[CH2:44]([C:24]1[N:25]([C:28]2[CH:43]=[CH:42][C:31]([O:32][C:33]3([CH2:38][OH:39])[CH2:34][CH2:35][CH2:36][CH2:37]3)=[CH:30][CH:29]=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]([CH2:46][CH2:47][CH3:48])[N:23]=1)[CH3:45]

Komponenten

8

Edukt 3

HCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 57460881HCID 57460881, Verbindung

Produkt 1

HCID 574608824'-{[2-Ethyl-1-(4-{[1-(hydroxymethyl)cyclopentyl]oxy}phenyl)-6-oxo-4-propyl-1,6-dihydropyrimidin-5-yl]methyl}biphenyl-2-carbonitrileAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 313Hydrochloric AcidLösungsmittelHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of sodium borohydride (0.39 g) in methanol (10 mL)-tetrahydrofuran (10 mL) was added calcium chloride (0.57 g) under ice-cooling, and the mixture was stirred for 15 min. A solution of methyl 1-{4-[5-[(2′-cyanobiphenyl-4-yl)methyl]-2-ethyl-6-oxo-4-propylpyrimidin-1(6H)-yl]phenoxy}cyclopentanecarboxylate (0.94 g) in tetrahydrofuran (10 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. The mixture was 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 (0.83 g, 93%) as a colorless solid.

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-1c0620e846394161b34df325ad3e7a5c
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07803940B2

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