Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylate → (4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanol

HRID 524024

Reaktionsgleichung

Reaktionsgleichung von HRID 524024
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][NH:8][C:9]1[C:14]([C:15](OCC)=[O:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=1>C1COCC1>[CH3:7][NH:8][C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([S:20][CH3:21])[N:10]=1

Komponenten

4

Edukt 2

HCID 295697Ethyl 4-(methylamino)-2-(methylsulfanyl)pyrimidine-5-carboxylateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 10679092(4-(Methylamino)-2-(methylthio)pyrimidin-5-yl)methanolAusbeute 86,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of lithium aluminum hydride (LiAlH4) (1.140 g, 30 mmol) in THF (100 mL) was added ethyl 4-(methylamino)-2-(methylthio)pyrimidine-5-carboxylate (4.536 g, 20 mmol), and the reaction mixture was stirred at room temperature for 2 hours. The solution was carefully quenched with H2O (2 mL), sodium hydroxide (NaOH) (aq., 15%, 2 mL) and additional H2O (7 mL), and then stirred for 1 hour. The mixture was extracted with EtOAc (2×100 mL), and the combined organic layers were washed with water and brine, dried over sodium sulfate, and concentrated to give (4-(methylamino)-2-(methylthio)pyrimidin-5-yl)methanol (3.2 g, 85%) as a yellowish solid. MS (ES+) C7H11N3OS requires: 185. found: 186 [M+H]+.

Aufarbeitung

  1. customThe solution was carefully quenched with H2O (2 mL), sodium hydroxide (NaOH) (aq., 15%, 2 mL) and additional H2O (7 mL)
  2. stirringstirred for 1 hour
  3. extractionThe mixture was extracted with EtOAc (2×100 mL)
  4. washthe combined organic layers were washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-6654faf946fa4e3aa815d5961975721e
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340514B2

Verknüpfte Notizen

Wird geladen…