Methyl 3-aminopyrazinecarboxylate → Methyl 3-amino-6-iodopyrazine-2-carboxylate

HRID 1048746

Reaktionsgleichung

Reaktionsgleichung von HRID 1048746
[I:1]N1C(=O)CCC1=O.[NH2:9][C:10]1[C:11]([C:16]([O:18][CH3:19])=[O:17])=[N:12][CH:13]=[CH:14][N:15]=1>CN(C)C=O>[NH2:9][C:10]1[C:11]([C:16]([O:18][CH3:19])=[O:17])=[N:12][C:13]([I:1])=[CH:14][N:15]=1

Komponenten

4

Edukt 2

HCID 72669Methyl 3-aminopyrazinecarboxylateHCID 120273N-Iodosuccinimide2×

Produkt 1

HCID 11087124Methyl 3-amino-6-iodopyrazine-2-carboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

1.5 equivalents of N-iodosuccinimide are added at room temperature to 5 g (32.7 mmol) of a methyl 3-aminopyrazine-2-carboxylate solution in 25 ml of dimethylformamide. The reaction medium is heated at 65° C. for 1 hour, added together with 0.5 equivalents of N-iodosuccinimide and maintained at 65° C. for 24 hours. After returning to room temperature, the solvent is evaporated and then the product is extracted several times with dichloromethane. The organic phases are combined, washed with 10% sodium bisulfite solution, dried on magnesium sulfate and concentrated to yield 8 g (88%) of methyl 3-amino-6-iodopyrazine-2-carboxylate in the form of a yellow solid.

Aufarbeitung

  1. temperaturemaintained at 65° C. for 24 hours
  2. customAfter returning to room temperature
  3. customthe solvent is evaporated
  4. extractionthe product is extracted several times with dichloromethane
  5. washwashed with 10% sodium bisulfite solution
  6. customdried on magnesium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-595a4a987c054d4fa6209b857f337209
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09381195B2

Verknüpfte Notizen

Wird geladen…