Toluene → [4-(4-Fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)pyrimidin-5-yl]methanol

HRID 253045Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 253045
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([C:14](OC)=[O:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([S:21][CH3:22])[N:9]=2)=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.[H-].C([Al+]CC(C)C)C(C)C>O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH2:14][OH:15])=[C:12]([CH:18]([CH3:20])[CH3:19])[N:11]=[C:10]([S:21][CH3:22])[N:9]=2)=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 1140TolueneHCID 11652673Methyl 4-(4-Fluorophenyl)-6-isopropyl-2-(methylthio)pyrimidine-5-carboxylate2×HCID 21225700Diisobutylaluminumhydride

Produkt 1

HCID 29980411[4-(4-Fluorophenyl)-2-(methylsulfanyl)-6-(propan-2-yl)pyrimidin-5-yl]methanolAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

20 g (62.5 mmol) of methyl 4-(4′-fluorophenyl)-6-isopropyl-2-methylthio-pyrimidin-5-yl-carboxylate (10) and 300 mL of dry anhydrous toluene were loaded in a IL three-neck round bottomed flask, equipped with a mechanical stirrer and an air duct, and stirred under a nitrogen atmosphere. 100 mmol of diisobutyl aluminum hydride (DIBAI-H) was then added in batches into the mixture while cooling in an ice-salt bath. After TLC assay showed that the starting compound (10) was depleted, the reaction mixture was warmed up to room temperature and further reacted for 2-3 hours. 500 mL of water was then added, and the organic layer was collected, washed with water (200 mL×2) and a saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate. The mixture was then filtered, evaporated under reduced pressure to remove the solvent, and recrystallized in ethyl acetate, obtaining 16 g of a white crystal, yield 88%.

Aufarbeitung

  1. customequipped with a mechanical stirrer
  2. temperaturewhile cooling in an ice-salt bath
  3. customfurther reacted for 2-3 hours
  4. customthe organic layer was collected
  5. washwashed with water (200 mL×2)
  6. dry with materiala saturated solution of sodium chloride (200 mL×1), and then dried overnight over anhydrous magnesium sulfate
  7. filtrationThe mixture was then filtered
  8. customevaporated under reduced pressure
  9. customto remove the solvent
  10. customrecrystallized in ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-7257b2d4602b46a994bc0a277aa5b486
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872012B2

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