Triethylamine → 2-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 32554
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.[CH3:24][Si:25]([C:28]#[CH:29])([CH3:27])[CH3:26].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[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:29]#[C:28][Si:25]([CH3:27])([CH3:26])[CH3:24]

Komponenten

6

Edukt 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 100687782-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

Produkt 1

HCID 691941732-{1-Methyl-4-phenyl-2-[(trimethylsilyl)ethynyl]-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amineAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-(2-Bromo-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Example 26) (52 mg), PdCl2dppf (10 mg), copper(I) iodide (2 mg), trimethylsilyl acetylene (0.11 mL) and triethylamine (0.2 mL) were heated in DMF (4 mL) at 80° C. for 1 hour under an inert atmosphere. The reaction mixture was concentrated in vacuo, EtOAc (20 mL)/MeOH (0.3 mL)/water (10 mL) added and the aqueous layer removed. The organic layer was dried (MgSO4), filtered, concentrated in vacuo, then purification by flash chromatography on silica eluting with 4% MeOH/DCM gave the title compound as a light brown solid (48 mg, 100%);

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated in vacuo, EtOAc (20 mL)/MeOH (0.3 mL)/water (10 mL)
  2. additionadded
  3. customthe aqueous layer removed
  4. dry with materialThe organic layer was dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. custompurification by flash chromatography on silica eluting with 4% MeOH/DCM

Quellen und Nachweise

ORD-Eintrag
ord-35832882817c42b5ad3d5c90ce30dd2d
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07427616B2

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