Allylamine → 2-Allylamino-4-ethylamino-7-methylthieno[3,2-d]pyrimidine

HRID 1250634

Reaktionsgleichung

Reaktionsgleichung von HRID 1250634
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH3:14])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:15]([NH2:18])[CH:16]=[CH2:17].C(=O)([O-])O.[Na+]>>[CH2:15]([NH:18][C:2]1[N:3]=[C:4]([NH:12][CH2:13][CH3:14])[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:16]=[CH2:17]

Komponenten

4

Edukt 3

HCID 7853AllylamineHCID 516892Sodium BicarbonateHCID 183264032-Chloro-4-ethylamino-7-methylthieno[3,2-d]pyrimidine

Produkt 1

HCID 183264772-Allylamino-4-ethylamino-7-methylthieno[3,2-d]pyrimidineAusbeute 64,3 %

Versuchsvorschrift

In a sealed tube were heated 273 mg (1.2 mmol) of 2-chloro-4-ethylamino-7-methylthieno[3,2-d]pyrimidine and 1.10 g (19.2 mmol) of allylamine at 160° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, and a saturated aqueous sodium hydrogen carbonate solution was added thereto, followed by extraction with ethyl acetate (50 ml×2). The organic layer was washed with brine and dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/2) to give 191 mg (yield: 64.3%) of the title compound.

Aufarbeitung

  1. customAfter completion of the reaction
  2. customto resume room temperature
  3. extractionfollowed by extraction with ethyl acetate (50 ml×2)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-f75b6658b69f41e5b67981c2462e5f32
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06339089B2

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