Diethyl ethylmalonate → 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone

HRID 1463233

Reaktionsgleichung

Reaktionsgleichung von HRID 1463233
O.Cl.[C:3]([NH2:11])(=[NH:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.C[O-].[Na+].[CH2:15]([CH:17]([C:23](OCC)=[O:24])[C:18](OCC)=[O:19])[CH3:16]>CO>[CH2:15]([C:17]1[C:18](=[O:19])[NH:10][C:3]([C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=2)=[N:11][C:23]=1[OH:24])[CH3:16]

Komponenten

5

Edukt 3

HCID 8610Diethyl ethylmalonateHCID 10942334Sodium MethoxideHCID 16219042Benzamidine HCl hydrate

Produkt 1

HCID 196906695-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinoneAusbeute 51 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A mixture of 45.19 g (0.29 mol) of benzamidine hydrochloride hydrate, 127.42 g (0.59 mol) of 25% sodium methoxide in methanol, 55 mL (0.29 mol) of diethyl ethylmalonate and 175 mL of methanol was heated at reflux for 25 h. The mixture was rotovapped to remove the bulk of the methanol. The residue was diluted with 300 mL of water and the pH was adjusted to 7 with concentrated hydrochloric acid. The solid precipitate was collected by filtration and dried under vacuum at 50° C. to afford 31.89 g (51%) of crude 5-ethyl-6-hydroxy-2-phenyl-4(3H)-pyrimidinone as a pale yellow solid. 1H-NMR (d6-DMSO) δ1.05(3H,t), 2.39(2H,q), 7.5(3H,m), 8.1(2H,m).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 25 h
  3. customto remove the bulk of the methanol
  4. additionThe residue was diluted with 300 mL of water
  5. filtrationThe solid precipitate was collected by filtration
  6. customdried under vacuum at 50° C.

Quellen und Nachweise

ORD-Eintrag
ord-5b496d12dab642ceadfa818b59c9765d
Quelldatensatz
uspto-grants-1994_04
Patentnummer
US05300477

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