Hydrazine → 3-Amino-6-chloro-5-hydrazino-pyrazine-2-carboxylic acid methyl ester

HRID 1274145

Reaktionsgleichung

Reaktionsgleichung von HRID 1274145
[NH2:1][C:2]1[C:3]([C:10]([O:12][CH3:13])=[O:11])=[N:4][C:5]([Cl:9])=[C:6](Cl)[N:7]=1.[NH2:14][NH2:15].CO.C(Cl)Cl>C(O)(C)(C)C.CN(C=O)C>[CH3:13][O:12][C:10]([C:3]1[C:2]([NH2:1])=[N:7][C:6]([NH:14][NH2:15])=[C:5]([Cl:9])[N:4]=1)=[O:11]

Komponenten

6

Edukt 3

HCID 9321HydrazineHCID 73828Methyl 3-amino-5,6-dichloropyrazine-2-carboxylateHCID 21226129Dichloromethane methanol

Produkt 1

HCID 541673563-Amino-6-chloro-5-hydrazino-pyrazine-2-carboxylic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6386tert-ButanolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Methyl 3-amino-5,6-dichloro-2-pyrazinecarboxylate (1.10 g, 5 mmol) was dissolved in 20 mL of tert-butyl alcohol and DMF (v/v; 1:1). Anhydrous hydrazine (0.18 mL, 5.5 mmol) and N,N'-diisopropylethyl amine (4.5 mL, 25 mmol) were then added sequentially at 25° C. The resulting mixture was stirred at 25° C. for 12 h. The reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL). The organic layer was dried (Na2SO4), filtered, and concentrated in vacuo to give a brown solid residue. This residue was used in the next-step reaction without further purification: TLC (Rf =0.53; 10% MeOH/CH2Cl2).

Aufarbeitung

  1. customThe reaction mixture was then partitioned between EtOAc (100 mL) and sat. NaCl (aq) (100 mL)
  2. dry with materialThe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto give a brown solid residue
  6. customThis residue was used in the next-step reaction without further purification

Quellen und Nachweise

ORD-Eintrag
ord-3df39bd3e3f941c2a6a496870cdbcb92
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06156758

Verknüpfte Notizen

Wird geladen…