Reaktion #42898

Reaktionsgleichung

HCl

6-Chloronicotinoyl chloride

6-hydroxynicotinic acid

5,6-diamino-1,3-dipropyluracil

→

solid

1,3-dipropyl-8-(6-chloro-3-pyridyl)xanthine

Lösungsmittel

CH2Cl2

NaOH

Water

pyridine

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction was warmed to room temperature
2. 2
   Sonstigeto quench
3. 3
   Sonstigethe reaction
4. 4
   SonstigeThe solvent was evaporated
5. 5
   Sonstigeto afford a dark colored oil
6. 6
   TemperaturAfter cooling
7. 7
   SonstigeA solid formed
8. 8
   Sonstigewas collected
9. 9
   Waschenwashed with water (20 ml), ether (20 ml) and chloroform (20 ml)

Vorschrift

6-Chloronicotinoyl chloride, prepared from 6-hydroxynicotinic acid (1.44 g, 10.4 mmol), in CH2Cl2 (20 ml) was added dropwise to a solution of 5,6-diamino-1,3-dipropyluracil (1.81 g, 8 mmol) in dry pyridine (8.2 ml) maintained at 5° C. The reaction was warmed to room temperature and stirred for an additional 3 hours. Water (50 ml) was added to quench the reaction. The solvent was evaporated to afford a dark colored oil. The oil was refluxed for 2 h in 2N NaOH (20 ml). After cooling, the pH was carefully adjusted to 7 with concentrated HCl. A solid formed and was collected and washed with water (20 ml), ether (20 ml) and chloroform (20 ml) to provide an off-white solid (1.9 g). The product was used in the next step without further purification.

Quelle