Hydrochloric Acid → Ethyl 8-allyl-5-hydroxy-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

HRID 224713

Reaktionsgleichung

Reaktionsgleichung von HRID 224713
C(O[C:4]([C:6]1[C:7]([NH:18][CH2:19][CH:20]=[CH2:21])=[N:8][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:10][CH:11]=1)=[O:5])C.C([CH:24]([C:28](Cl)=[O:29])[C:25](Cl)=[O:26])C.O.Cl.[CH2:33]([O:35]CC)[CH3:34]>C(O)C>[CH2:33]([O:35][C:28]([C:24]1[C:25](=[O:26])[N:18]([CH2:19][CH:20]=[CH2:21])[C:7]2[N:8]=[C:9]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[N:10]=[CH:11][C:6]=2[C:4]=1[OH:5])=[O:29])[CH3:34]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 3283Diethyl EtherHCID 2767635Ethyl 4-(allylamino)-2-phenyl-5-pyrimidinecarboxylateHCID 109209242-Ethylpropanedioyl dichloride

Produkt 1

HCID 54726500Ethyl 8-allyl-5-hydroxy-7-oxo-2-phenyl-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To 16.3 g. (0.057 mole) of 4-(2-propenylamino)-2-phenyl-5-pyrimidine carboxylic acid ethyl ester in diethyl ether was added 4.3 g. (0.029 mole) of ethyl malonyl chloride and then stirred 3 hours at room temperature. The reaction was then filtered and stripped to dryness and the residue was added to a solution of 1.3 g. (0.057 mole) of Na in ethanol and stirred at room temperature for 10 minutes. Water was added until the reaction became clear and then acidified with HCl. This solution was chilled in ice and the resulting solid was removed by filtration. Recrystallization from ethyl acetate gave 0.55 g. of title product with m.p. 174°-175° C.

Aufarbeitung

  1. filtrationThe reaction was then filtered
  2. additionthe residue was added to a solution of 1.3 g
  3. temperatureThis solution was chilled in ice
  4. customthe resulting solid was removed by filtration
  5. customRecrystallization from ethyl acetate
  6. customgave 0.55 g

Quellen und Nachweise

ORD-Eintrag
ord-3b83da16b791456da4b115997fb00fe5
Quelldatensatz
uspto-grants-1980_11
Patentnummer
US04233446

Verknüpfte Notizen

Wird geladen…