Dimethylamine → 6-chloro-N,N-dimethyl-5-nitropyrimidin-4-amine

HRID 377508

Reaktionsgleichung

Reaktionsgleichung von HRID 377508
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[CH3:12][NH:13][CH3:14].C(N(C(C)C)CC)(C)C>C(Cl)Cl>[CH3:12][N:13]([CH3:14])[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 674DimethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 81531Diisopropylethylamine

Produkt 1

HCID 71136226-chloro-N,N-dimethyl-5-nitropyrimidin-4-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
-70 °C

Versuchsvorschrift

Dissolve 50 g (0.26 mol) of 4,6-dichloro-5-nitropyrimidine in 500 mL of CH2Cl2 and cool to -70° C. Add a solution of 24 mL (0.28 mol) dimethylamine, 70 mL (0.40 mol) of diisopropylethylamine, and 100 mL of CH2Cl2 over 30 minutes. Warm to ambient temperature and wash the reaction mixture with 500 mL of 20% K2CO3. Dry the CH2Cl2 portion over MgSO4, treat with charcoal filter, and remove the filtrate under vacuum. Crystallize the residue with ether to provide 4-dimethylamino-6-chloro-5-nitropyrimidine.

Aufarbeitung

  1. temperatureWarm to ambient temperature
  2. washwash the reaction mixture with 500 mL of 20% K2CO3
  3. dry with materialDry the CH2Cl2 portion over MgSO4
  4. additiontreat with charcoal
  5. filtrationfilter
  6. customremove the filtrate under vacuum
  7. customCrystallize the residue with ether

Quellen und Nachweise

ORD-Eintrag
ord-ce50dedc3d6a49e4ad3462d40aaac1ad
Quelldatensatz
uspto-grants-2000_02
Patentnummer
US06025489

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