Potassium borohydride → [2-(Pyridin-2-ylamino)thiazol-5-yl]methanol

HRID 1985751

Reaktionsgleichung

Reaktionsgleichung von HRID 1985751
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH:13]=[O:14])=[CH:11][N:12]=1.[BH4-].[K+]>C(O)C.CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[NH:7][C:8]1[S:9][C:10]([CH2:13][OH:14])=[CH:11][N:12]=1

Komponenten

5

Edukt 2

HCID 4192641Potassium borohydrideHCID 220190582-(Pyridin-2-ylamino)thiazole-5-carbaldehyde

Produkt 1

HCID 22019159[2-(Pyridin-2-ylamino)thiazol-5-yl]methanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(pyridin-2-ylamino)thiazole-5-carbaldehyde (410 mg, 2 mmol) in ethanol (15 mL) and DMF (5 mL) was added potassium borohydride (120 mg). The resulting mixture was stirred at RT for 1 h, quenched with 10% sulfuric acid solution and concentrated in vacuo. The residue was extracted with methanol and the methanol solution was concentrated. The crude material was diluted with water, filtered and the solid was washed with water and dried in vacuo to provide compound 9A, [2-(pyridin-2-ylamino)thiazol-5-yl]methanol (385 mg, 93%) as a solid. LC/MS; (M+H)+=208

Aufarbeitung

  1. customquenched with 10% sulfuric acid solution
  2. concentrationconcentrated in vacuo
  3. extractionThe residue was extracted with methanol
  4. concentrationthe methanol solution was concentrated
  5. additionThe crude material was diluted with water
  6. filtrationfiltered
  7. washthe solid was washed with water
  8. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-b1fd8bfc2b364e8dbe2e2bbfe0359bf3
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07547711B2

Verknüpfte Notizen

Wird geladen…