Potassium Carbonate → 7-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidine

HRID 32551Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32551
Br[C:2]1[N:3]([CH3:24])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([O:22][CH3:23])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.[S:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C(=O)([O-])[O-].[K+].[K+].[O-]S([O-])(=O)=O.[Mg+2]>C1(C)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].CO>[CH3:23][O:22][C:19]1[C:20]2[N:21]=[C:13]([C:4]3[N:3]([CH3:24])[C:2]([C:27]4[CH:28]=[CH:29][S:25][CH:26]=4)=[N:6][C:5]=3[C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:14][C:15]=2[N:16]=[CH:17][N:18]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 24083Sulfuric acid magnesium salt (1:1)HCID 581760Thiophene-3-boronic acidHCID 691972172-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine2×

Produkt 1

HCID 691963357-Methoxy-2-[1-methyl-4-phenyl-2-(3-thienyl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidineAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)KatalysatorHCID 887MethanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)-7-methoxy[1,3]thiazolo[5,4-d]pyrimidine (Intermediate 43) (50 mg), [1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (14 mg), thiophene-3-boronic acid (17 mg) and 2M potassium carbonate (0.25 mL) were heated in toluene (5 mL)/MeOH (1 mL) at 100° C. under an inert atmosphere. After 90 minutes the reaction mixture was cooled to ambient temperature, MgSO4 added, filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 35% EtOAc/iso-hexane gave the title compound as a colourless solid (40 mg, 82%);

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customPurification by flash chromatography on silica eluting with 35% EtOAc/iso-hexane

Quellen und Nachweise

ORD-Eintrag
ord-80e7cc6287fd4e30b403aebe9cd0fd2b
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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