Sodium hydride → (2R,3R)-3-([6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)butan-2-ol

HRID 1175342Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1175342
[CH3:1][C@@H:2]([OH:6])[C@H:3]([OH:5])[CH3:4].[Cl:7][C:8]1[CH:13]=[C:12](Cl)[N:11]=[C:10]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:9]=1.[H-].[Na+]>O1CCCC1>[Cl:7][C:8]1[N:9]=[C:10]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[C:18]=2[F:24])[N:11]=[C:12]([O:5][C@H:3]([CH3:4])[C@H:2]([OH:6])[CH3:1])[CH:13]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 225936(2R,3R)-ButanediolHCID 859280374,6-Dichloro-2-((2,3-difluorobenzyl)thio)pyrimidine

Produkt 1

HCID 86619864(2R,3R)-3-([6-chloro-2-[(2,3-difluorobenzyl)thio]pyrimidin-4-yl}oxy)butan-2-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of (2R,3R)-butane-2,3-diol (250 mg) and 4,6-Dichloro-2-[(2,3-difluorobenzyl)thio]pyrimidine (the product of example 1 step (ii)) (427 mg) in anhydrous tetrahydrofuran (20 ml) at ambient temperature was added 60% sodium hydride (33.4 mg). After stirring for 15 minutes the reaction mixture was partitioned between aq. ammonium chloride solution and ethyl acetate. The organics collected, dried (MgSO4) and solvents removed under vacuo to give the subtitle compound as colourless gum. Yield: 525 mg.

Aufarbeitung

  1. customwas partitioned between aq. ammonium chloride solution and ethyl acetate
  2. dry with materialThe organics collected, dried (MgSO4) and solvents
  3. customremoved under vacuo

Quellen und Nachweise

ORD-Eintrag
ord-4b2699db919b41928e50983680c23139
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838675B2

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