Imidazole → HCID 58507769, Verbindung

HRID 1408462Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1408462
[O:1]1[CH2:6][CH2:5][N:4]([C:7]2[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=[C:11]([C:13]3[CH:14]=[C:15]([OH:19])[CH:16]=[CH:17][CH:18]=3)[N:12]=2)[CH2:3][CH2:2]1.N1C=CN=C1.[CH3:28][C:29]([Si:32](Cl)([CH3:34])[CH3:33])([CH3:31])[CH3:30]>CN(C=O)C>[Si:32]([O:19][C:15]1[CH:14]=[C:13]([C:11]2[N:12]=[C:7]([N:4]3[CH2:3][CH2:2][O:1][CH2:6][CH2:5]3)[C:8]3[S:22][CH:21]=[CH:20][C:9]=3[N:10]=2)[CH:18]=[CH:17][CH:16]=1)([C:29]([CH3:31])([CH3:30])[CH3:28])([CH3:34])[CH3:33]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 99013723-(4-Morpholin-4-ylthieno[3,2-d]pyrimidin-2-yl)phenol

Produkt 1

HCID 58507769HCID 58507769, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

3-(4-morpholinothieno[3,2-d]pyrimidin-2-yl)phenol [synthesized according to Hayakawa et al., Bioorganic & Med. Chem. 14:6847-6858 (2006)] (540 mg, 1.72 mmol, 1.0 eq.) was dissolved in DMF (5 ml). To this imidazole (936 mg, 13.8 mmol, 8.0 eq.) and TBDMSCl (909 mg, 6.02 mmol, 3.5 eq.) were added and the mixture was heated at 70° C. for 3 h. DMF was evaporated under reduced pressure and purification by flash chromatography (hexane:ethyl acetate, gradient from 100%-50% hexane in EtOAc) yielded the title compound as a white solid.

Aufarbeitung

  1. customDMF was evaporated under reduced pressure and purification by flash chromatography (hexane:ethyl acetate, gradient from 100%-50% hexane in EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-5b408368b72c4ed1b5dbe00273071794
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921361B2

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