Imidazole → HCID 91865194, Verbindung

HRID 985413

Reaktionsgleichung

Reaktionsgleichung von HRID 985413
N[C:2]1[CH:7]=[C:6]([CH2:8]O)[CH:5]=CN=1.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1.[CH3:15][C:16]([Si:19](Cl)(C)C)([CH3:18])[CH3:17].CN(C=[O:27])C>>[C:16]([SiH2:19][O:27][C:6]([CH3:5])([CH3:8])[C:7]1[CH:13]=[CH:14][N:10]=[C:11]([NH2:12])[CH:2]=1)([CH3:18])([CH3:17])[CH3:15]

Komponenten

5

Edukt 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 1515296(2-Aminopyridin-4-yl)methanol

Produkt 1

HCID 91865194HCID 91865194, Verbindung

Versuchsvorschrift

(2-Amino-pyridin-4-yl)-methanol (4.68 g, 37.7 mmol) was dissolved in 40 mL anhydrous DMF under N2. Imidazole (2.57 g, 37.7 mmol, 1 equiv) was added followed by the addition of TBSCl (5.68 g, 37.7 mmol, 1 equiv). After 2 hours the reaction was quenched by the addition of water. A precipitate formed which was filtered to afford pure desired product. The aqueous filtrate was extract 3× with EtOAc. The organic phases were dried over Na2SO4, filtered and concentrated to afford additional impure material. 1H NMR (CDCl3) δ 7.99 (d, 1H, J=5.8 Hz), 6.57 (d, 1H, J=5.1 Hz), 6.51 (s, 1H), 4.64 (s, 2H), 4.40 (bs, 2H), 0.95 (s, 9H), 0.11 (s, 6H). 2-[4-(tert-Butyl-dimethyl-silanyloxymethyl)-pyridin-2-ylamino]-thiazole-5-carbonitrile (3-1)

Aufarbeitung

  1. customAfter 2 hours the reaction was quenched by the addition of water
  2. customA precipitate formed which
  3. filtrationwas filtered

Quellen und Nachweise

ORD-Eintrag
ord-f1372496021441a7b004c13642ea5052
Quelldatensatz
uspto-grants-2005_03
Patentnummer
US06872724B2

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