Ammonia → Methyl 6-amino-2-chloropyrimidine-4-carboxylate

HRID 495029

Reaktionsgleichung

Reaktionsgleichung von HRID 495029
[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9](S(C)(=O)=O)[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4].[NH3:16]>O1CCOCC1.CO>[CH3:1][O:2][C:3]([C:5]1[CH:10]=[C:9]([NH2:16])[N:8]=[C:7]([Cl:15])[N:6]=1)=[O:4]

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 84031284Methyl 2-chloro-6-(methylsulfonyl)pyrimidine-4-carboxylate

Produkt 1

HCID 53396493Methyl 6-amino-2-chloropyrimidine-4-carboxylateAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

2-Chloro-6-methanesulfonylpyrimidine-4-carboxylic acid methyl ester (3.7 g, 14.75 mmol) was dissolved in dioxane and 7N ammonia in methanol was added. The reaction mixture was stirred at room temperature for 3 hours, concentrated under vacuum, and the residue partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by column chromatography to provide 6-amino-2-chloropyrimidine-4-carboxylic acid methyl ester (2.35 g, 85% yield): 1H NMR (DMSO-d6): δ 7.6 (br s, 1H), 7.00 (s, 1H), 3.84 (s, 3H), 3.33 (s, 3H).

Aufarbeitung

  1. concentrationconcentrated under vacuum
  2. customthe residue partitioned between ethyl acetate and water
  3. customThe organic phase was dried
  4. concentrationconcentrated
  5. customThe product was purified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-66fb0aa808b34c818b7117d066569607
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538214B2

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