Allylamine → 2,4,7-Triallylaminothieno[3,2-d]pyrimidine

HRID 1250694Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1250694
[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([NH:15][CH2:16][CH:17]=[CH2:18])[C:8]2[S:13][CH:12]=[C:11](Br)[C:9]=2[N:10]=1)[CH:2]=[CH2:3].[CH2:19]([NH2:22])[CH:20]=[CH2:21].C(=O)([O-])[O-].[K+].[K+]>[Cu]>[CH2:1]([NH:4][C:5]1[N:6]=[C:7]([NH:15][CH2:16][CH:17]=[CH2:18])[C:8]2[S:13][CH:12]=[C:11]([NH:22][CH2:19][CH:20]=[CH2:21])[C:9]=2[N:10]=1)[CH:2]=[CH2:3]

Komponenten

5

Edukt 3

HCID 7853AllylamineHCID 11430Potassium CarbonateHCID 183264202,4-Diallylamino-7-bromothieno[3,2-d]pyrimidine

Produkt 1

HCID 183264232,4,7-Triallylaminothieno[3,2-d]pyrimidineAusbeute 72,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23978CopperKatalysator

Versuchsvorschrift

120 mg (0.37 mmol) of 2,4-diallylamino-7-bromothieno[3,2-d]pyrimidine, 337 mg (5.9 mmol) of allylamine, 56 mg (0.41 mmol) of potassium carbonate and 1 mg of copper were heated in a sealed tube at 180° C. for 5 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by distilling off excess allylamine under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8) to give 81 mg (yield: 72.9%) of the title compound.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. distillationby distilling off excess allylamine under reduced pressure
  4. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/8)

Quellen und Nachweise

ORD-Eintrag
ord-94761747e999438f8e52170d0b8bc2f7
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

Notizen zur Reaktion

Wird geladen…