Diethyl allylmalonate → 5-Allylpyrimidine-4,6-diol

HRID 82247

Reaktionsgleichung

Reaktionsgleichung von HRID 82247
C([O:3][C:4](=O)[CH:5]([CH2:11][CH:12]=[CH2:13])[C:6](OCC)=[O:7])C.C[O-].[Na+].C(O)(=O)C.[CH:22]([NH2:24])=[NH:23]>C(O)C>[CH2:11]([C:5]1[C:6](=[O:7])[NH:24][CH:22]=[N:23][C:4]=1[OH:3])[CH:12]=[CH2:13]

Komponenten

5

Edukt 3

HCID 74900Diethyl allylmalonateHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Produkt 1

HCID 254215755-Allylpyrimidine-4,6-diolAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

2-Allyl-malonic acid diethyl ester (Preparation 205, 100 g, 0.5 mol) was added dropwise to a mixture of sodium methoxide (27 g, 0.5 mol) in ethanol (1 L) at 0-5° C. and the mixture was stirred at this temperature for 10 min. Formamidine acetate (51.9 g, 0.5 mol) was added and the mixture was stirred at room temperature overnight. The solvent was removed in vacuo, and aqueous hydrochloric acid (36.5%) and water were added to adjust the pH to approximately 3 at 0-20° C. The resulting mixture was filtered to afford the title compound as a colorless solid in 57% yield, 87.12 g.

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe solvent was removed in vacuo, and aqueous hydrochloric acid (36.5%) and water
  3. additionwere added
  4. customat 0-20° C
  5. filtrationThe resulting mixture was filtered

Quellen und Nachweise

ORD-Eintrag
ord-8d9eb956cc6845f2a0afad3fa487d257
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846698B2

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