4-Chloro-5-iodo-2-(methylthio)pyrimidine → (4-Chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol

HRID 81745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 81745
[Cl:1][C:2]1[C:7](I)=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1.C([Mg]Br)(C)C.[CH:16]([C:19]1[CH:26]=[C:25]([O:27][CH3:28])[C:24]([O:29][CH3:30])=[CH:23][C:20]=1[CH:21]=[O:22])([CH3:18])[CH3:17]>C1COCC1>[Cl:1][C:2]1[C:7]([CH:21]([C:20]2[CH:23]=[C:24]([O:29][CH3:30])[C:25]([O:27][CH3:28])=[CH:26][C:19]=2[CH:16]([CH3:18])[CH3:17])[OH:22])=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Komponenten

5

Edukt 3

HCID 136365194-Chloro-5-iodo-2-(methylthio)pyrimidineHCID 541451142-Isopropyl-4,5-dimethoxy-benzaldehydeHCID 178418365HCID 178418365, Verbindung

Produkt 1

HCID 59598617(4-Chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanolAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 4-chloro-5-iodo-2-methylsulfanyl-pyrimidine (1.10 g, 3.9 mmol) in 20 mL THF at −40° C. was added isopropyl magnesium bromide (2.3 mL, 2 M in THF)) over 5 minutes. After 30 minutes, 2-isopropyl-4,5-dimethoxy-benzaldehyde from step 3 (1.04 g, 4.6 mmol) was added and the solution was warmed to room temperature. The mixture was quenched by the addition of brine, and extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification via flash chromatography (ethyl acetate) afforded (4-chloro-2-methylsulfanyl-pyrimidin-5-yl)-(2-isopropyl-4,5-dimethoxy-phenyl)-methanol (1.168 g, 82%) as a light yellow solid.

Aufarbeitung

  1. customThe mixture was quenched by the addition of brine
  2. extractionextracted with CH2Cl2
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification via flash chromatography (ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-3ee0335c6f604df2af242e06b36fffd2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846705B2

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