Acetic Anhydride → N-(6-aminopyrimidin-4-yl)acetamide

HRID 2366202

Reaktionsgleichung

Reaktionsgleichung von HRID 2366202
[N:1]1[C:6]([NH2:7])=[CH:5][C:4]([NH2:8])=[N:3][CH:2]=1.[C:9](OC(=O)C)(=[O:11])[CH3:10]>O1CCOCC1>[NH2:8][C:4]1[N:3]=[CH:2][N:1]=[C:6]([NH:7][C:9](=[O:11])[CH3:10])[CH:5]=1

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 79608Pyrimidine-4,6-diamine

Produkt 1

HCID 3031498N-(6-aminopyrimidin-4-yl)acetamideAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a stirred suspension of pyrimidine-4,6-diamine (500 mg, 4.55 mmol) in dioxane (20 mL) was added acetic anhydride (465 mg, 4.55 mmol) and the resulting mixture was heated under reflux for 15 hours. The reaction was cooled to room temperature and the resulting precipitate was collected by filtration. The filtercake was dissolved in 1N HCl and the pH of the aqueous phase adjusted to 7 by the addition of 1N NaOH. The resulting white precipitate was collected by filtration and dried to afford the desired product as a white solid (420 mg, 61% yield). LCMS (ESI) m/z: 152.0 [M+H+].

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 15 hours
  3. filtrationthe resulting precipitate was collected by filtration
  4. dissolutionThe filtercake was dissolved in 1N HCl
  5. additionthe pH of the aqueous phase adjusted to 7 by the addition of 1N NaOH
  6. filtrationThe resulting white precipitate was collected by filtration
  7. customdried

Quellen und Nachweise

ORD-Eintrag
ord-df25aac569e74280ab2451790da6bd3b
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08697708B2

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