2,4-Dimethoxybenzonitrile → 1H-Purine, 8-(2,4-dimethoxyphenyl)-

HRID 1155063

Reaktionsgleichung

Reaktionsgleichung von HRID 1155063
[NH2:1][C:2]1[C:7]([NH2:8])=[CH:6][N:5]=[CH:4][N:3]=1.[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[C:13]#N.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1>[CH3:9][O:10][C:11]1[CH:18]=[C:17]([O:19][CH3:20])[CH:16]=[CH:15][C:12]=1[C:13]1[NH:8][C:7]2[C:2](=[N:3][CH:4]=[N:5][CH:6]=2)[N:1]=1

Komponenten

5

Edukt 3

HCID 777502,4-DimethoxybenzonitrileHCID 837034,5-DiaminopyrimidineHCID 521998p-Toluenesulfonic acid monohydrate

Produkt 1

HCID 30599121H-Purine, 8-(2,4-dimethoxyphenyl)-

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 2 g of 4,5-diamino-pyrimidine, 4 g of 2,4-dimethoxy-benzonitrile, 6 g of p-toluene sulfonic acid hydrate, and 40 ml of benzene was heated, whereby the benzene was distilled off. The residue was heated for 30 minutes at 120° C. After cooling the residue was triturated with 2 N ammonia and extracted with ethyl acetate. The ethyl acetate phase was extracted with 2 N hydrochloric acid, the aqueous phase was neutralized and again extracted with ethyl acetate, and subsequently the organic phase was extracted with 2 N sodium hydroxide solution. When the aqueous phase was neutralized, the product was precipitated and recrystallized from water.

Aufarbeitung

  1. temperaturewas heated
  2. distillationwhereby the benzene was distilled off
  3. temperatureAfter cooling the residue
  4. customwas triturated with 2 N ammonia
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate phase was extracted with 2 N hydrochloric acid
  7. extractionagain extracted with ethyl acetate
  8. extractionsubsequently the organic phase was extracted with 2 N sodium hydroxide solution
  9. customthe product was precipitated
  10. customrecrystallized from water

Quellen und Nachweise

ORD-Eintrag
ord-63f0d60977ab4bd0987398e8ee4f424a
Quelldatensatz
uspto-grants-1981_11
Patentnummer
US04299834

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