Ethyl Acetate → 2-(Methylsulfanyl)pyrimidin-5-ol

HRID 386583

Reaktionsgleichung

Reaktionsgleichung von HRID 386583
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6](B2OC(C)(C)C(C)(C)O2)=[CH:5][N:4]=1.B1([O-])O[O:19]1.O.O.O.O.[Na+].CCOC(C)=O>C1COCC1.O>[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([OH:19])=[CH:5][N:4]=1

Komponenten

5

Edukt 3

HCID 8857Ethyl AcetateHCID 164142192-(Methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidineHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Produkt 1

HCID 5883572-(Methylsulfanyl)pyrimidin-5-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21881883Oxolane--water (1/1)Lösungsmittel

Versuchsvorschrift

To a stirring solution of 2-(methylthio)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine (from step A) (1.167 g, 4.63 mmol) in THF/H2O (20 mL 1:1) at room temperature under argon was added sodium perborate tetrahydrate (2.137 g, 13.9 mmol). The reaction mixture was stirred at room temperature overnight. The reaction was cooled to room temperature. EtOAc (10 mL) was added to the reaction mixture, which was washed with brine (15 mL×3). Organic phase was dried (MgSO4), filtered and concentrated. The crude product was very insoluble, therefore it was used directly to next step. MS (ESI) 143 (M+H).

Aufarbeitung

  1. temperatureThe reaction was cooled to room temperature
  2. washwas washed with brine (15 mL×3)
  3. dry with materialOrganic phase was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-85b7039681764b56b930fd22abf2fe66
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372837B2

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