Diphenyl Ether → 2,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine

HRID 1032816

Reaktionsgleichung

Reaktionsgleichung von HRID 1032816
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][C:4]=1[CH2:5][CH:6]([C:12]([CH3:14])=O)[C:7]([O:9]CC)=O.[NH2:21][C:22]1[N:27]=[C:26]([NH2:28])[CH:25]=[C:24]([NH2:29])[N:23]=1.C1(OC2C=CC=CC=2)C=CC=CC=1>O.C(O)C>[NH2:21][C:22]1[N:23]=[C:24]([NH2:29])[C:25]2[C:12]([CH3:14])=[C:6]([CH2:5][C:4]3[CH:15]=[C:16]([O:19][CH3:20])[CH:17]=[CH:18][C:3]=3[O:2][CH3:1])[C:7](=[O:9])[NH:28][C:26]=2[N:27]=1

Komponenten

5

Edukt 3

HCID 7583Diphenyl EtherHCID 138632,4,6-TriaminopyrimidineHCID 12597482Ethyl alpha-(2,5-dimethoxybenzyl)acetoacetate

Produkt 1

HCID 125974832,4-Diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidineAusbeute 65,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

A mixture of ethyl α-(2,5-dimethoxybenzyl)acetoacetate (21.2 g), 2,4,6-triaminopyrimidine (10 g) and diphenyl ether (100 ml) was heated at 190°-230° C. for 1.5 hours in an apparatus fitted with a Dean-Stark trap and water-ethanol (4 ml) was collected. Methanol (200 ml) and ethanol (50 ml) was added to the cooled reaction mixture. The resulting solid was collected by filtration and treated with boiling water (1 l) to give 2,4-diamino-5-methyl-6-(2,5-dimethoxybenzyl)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine (17 g), m.p. 325°-326° C.

Aufarbeitung

  1. temperaturewas heated at 190°-230° C. for 1.5 hours in an apparatus
  2. customwas collected
  3. additionMethanol (200 ml) and ethanol (50 ml) was added to the cooled reaction mixture
  4. filtrationThe resulting solid was collected by filtration
  5. additiontreated with boiling water (1 l)

Quellen und Nachweise

ORD-Eintrag
ord-d28c7a6fe3ec44aa9ad890d2a20edf2f
Quelldatensatz
uspto-grants-1990_09
Patentnummer
US04959474

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