Ethyl Acetate → 2-(1-Methyl-4-phenyl-2-pyridin-4-yl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32552
Br[C:2]1[N:3]([CH3:23])[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[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.[N:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Na+].[Na+].CCOC(C)=O>CN(C=O)C>[CH3:23][N:3]1[C:4]([C:13]2[S:14][C:15]3[N:16]=[CH:17][N:18]=[C:19]([NH2:22])[C:20]=3[N:21]=2)=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=[C:2]1[C:27]1[CH:28]=[CH:29][N:24]=[CH:25][CH:26]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 2734379(Pyridin-4-yl)boronic acidHCID 100687782-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Produkt 1

HCID 100914752-(1-Methyl-4-phenyl-2-pyridin-4-yl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amineAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (20 mg), PdCl2dppf (8 mg), pyridine-4-boronic acid (8 mg) and 2M sodium carbonate (2.0 mL) were heated in DMF (2.0 mL) at 100° C. under an inert atmosphere. After 3 hours the reaction mixture was cooled to ambient temperature, EtOAc (25 mL) added then washed with water (15 mL), brine (2×10 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography on silica eluting with 6% MeOH/DCM gave a dark brown solid which was washed with diethyl ether then dried under high vacuum to give the title compound as light brown solid (6 mg, 31%);

Aufarbeitung

  1. washthen washed with water (15 mL), brine (2×10 mL)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customPurification by flash chromatography on silica eluting with 6% MeOH/DCM
  6. customgave a dark brown solid which
  7. washwas washed with diethyl ether
  8. customthen dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b69896e4d4dc48c4befe8458f12be382
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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