2-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanol → 2-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanol

HRID 1255970

Reaktionsgleichung

Reaktionsgleichung von HRID 1255970
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16](F)=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:24])[CH:3]=1.C([Si](C)(C)[O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])(C)(C)C.C([Si](C)(C)OCCOC(O)C)(C)(C)C.C[Si](C)(C)[O-].[K+]>CS(C)=O>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([NH:9][C:10]2[C:19]3[C:14](=[CH:15][C:16]([O:30][CH2:31][CH2:32][O:33][CH2:34][CH2:35][OH:36])=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=3)[N:13]=[CH:12][N:11]=2)=[C:4]([F:24])[CH:3]=1

Komponenten

6

Edukt 4

HCID 111175822-(2-((Tert-butyldimethylsilyl)oxy)ethoxy)ethanolHCID 111761854-[(3,4-Dichloro-6-fluorophenyl)amino]-7-fluoro-6-nitroquinazoline2×HCID 23668039Potassium trimethylsilanolateHCID 86618841HCID 86618841, Verbindung

Produkt 1

HCID 692669552-{2-[4-(4,5-Dichloro-2-fluoro-phenylamino)-6-nitro-quinazoline-7-yloxy]-ethoxy}-ethanolAusbeute 24 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

(4,5-Dichloro-2-fluoro-phenyl-(7-fluoro-6-nitro-quinazolin-4-yl)-amine (Compound 25, 0.723 grams, 1.94 mmol), 2-[2-(tert-butyl-dimethyl -silanyloxy)-ethoxy]-ethanol (Compound 28a (0.64 grams, 2.9 mmol) and potassium trimethylsilanolate (0.75 gram, 5.83 mmol) were dissolved in dry DMSO (42 ml) and the resulting mixture was stirred under nitrogen atmosphere for 5 hours at 25° C. The obtained deep crimson mixture was thereafter extracted with ethyl acetate (EtOAc) and water, and the organic phase was washed with NaHCO3 (4%) and brine, and dried over Na2SO4. The solvent was then removed under reduced pressure and the residue was purified by silica gel column chromatography, using a mixture of 2% MeOH in CH2Cl2 as eluent, to obtain Compound 29a (0.217 gram, 24% yield).

Aufarbeitung

  1. extractionThe obtained deep crimson mixture was thereafter extracted with ethyl acetate (EtOAc) and water
  2. washthe organic phase was washed with NaHCO3 (4%) and brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was then removed under reduced pressure
  5. customthe residue was purified by silica gel column chromatography
  6. additiona mixture of 2% MeOH in CH2Cl2 as eluent

Quellen und Nachweise

ORD-Eintrag
ord-82e84905b8024401aa14f0e858ee0c02
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08461166B2

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