Ethyl Acetate → 7-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 58277Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 58277
[N:1]([CH:4]([C:6]1[N:7]=[C:8]2[S:21][CH:20]=[CH:19][N:9]2[C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5])=[N+]=[N-].CP(C)C.C(OCC)(=O)C>O1CCCC1.O>[NH2:1][CH:4]([C:6]1[N:7]=[C:8]2[S:21][CH:20]=[CH:19][N:9]2[C:10](=[O:18])[C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:5]

Komponenten

6

Edukt 3

HCID 8857Ethyl AcetateHCID 68983TrimethylphosphineHCID 866500747-(1-azidoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

Produkt 1

HCID 581114357-(1-aminoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a stirred solution of 7-(1-azidoethyl)-6-phenyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one (0.23 g, 0.77 mmol) in tetrahydrofuran (5 mL) and water (1 mL) was added 1.00 M of trimethylphosphine in tetrahydrofuran (0.93 mL, 0.93 mmol) at room temperature, and the mixture was stirred at room temperature for 1 hour. To the mixture was added ethyl acetate, and the mixture was extracted with aqueous 1 N HCl solution (three times). The combined extract was neutralized with solid NaHCO3 and extracted with dicloromethane (two times). The combined organic layer was washed with brine, dried over Na2SO4, and concentrated to give the desired compound (0.13 g, 62%). LCMS calculated for C14H14N3OS (M+H)+: m/z=272.1. Found: 272.0.

Aufarbeitung

  1. extractionthe mixture was extracted with aqueous 1 N HCl solution (three times)
  2. extractionThe combined extract
  3. extractionextracted with dicloromethane (two times)
  4. washThe combined organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-268aade604ba408dacc5cc4147ac1450
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434746B2

Notizen zur Reaktion

Wird geladen…