Reaktion #168589

ord-15d73fd7460a4f2aaac3477c717cc714

Reaktionsgleichung

S=C=Nc1ccccc1
Phenyl isothiocyanate
CC(C)Cn1c(NN)cc(=O)n(C)c1=O
6-hydrazinyl-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione
CC(C)Cn1c(=O)n(C)c(=O)c2c(Nc3ccccc3)[nH]nc21
product
Ausbeute 41.0%
CC(C)Cn1c(=O)n(C)c(=O)c2c(Nc3ccccc3)[nH]nc21
7-Isobutyl-5-methyl-3-(phenylamino)-2H-pyrazolo[3,4-d]pyrimidine-4,6(5H,7H)-dione
Ausbeute 41.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigeevaporated
  2. 2
    Sonstigeto remove solvent under reduced pressure
  3. 3
    SonstigeThe residue is further purified by silica-gel flash chromatography

Vorschrift

Phenyl isothiocyanate (0.17 mL, 1.4 mmol) is added to a solution of 6-hydrazinyl-1-isobutyl-3-methylpyrimidine-2,4(1H,3H)-dione (31 mg, 0.47 mmol) in DMF (10 mL). The reaction mixture is heated at 120° C. for 6 hours, and then evaporated to remove solvent under reduced pressure. The residue is further purified by silica-gel flash chromatography to give 20 mg of product (Yield: 41%). 1H NMR (400 MHz, DMSO-d6) δ0.95 (s, 3H), 0.97 (s, 3H), 2.30 (m, 1H), 3.37 (s, 3H), 3.77 (d, 2H), 7.16-7.43 (m, 5H), 7.61 (s, 1H). MS (FAB) m/z 314.3 [M+H]+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08846693B2uspto-grants-2014_09