Allylamine → 2-Allylamino-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine
Reaktionsgleichung
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1.[CH2:22]([NH2:25])[CH:23]=[CH2:24].C(=O)([O-])O.[Na+]>>[CH2:22]([NH:25][C:2]1[N:3]=[C:4]([NH:12][CH2:13]/[CH:14]=[CH:15]/[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:5]2[S:10][CH:9]=[C:8]([CH3:11])[C:6]=2[N:7]=1)[CH:23]=[CH2:24]Komponenten
4
Versuchsvorschrift
316 mg (1.0 mmol) of 2-chloro-4-(trans-cinnamylamino)-7-methylthieno[3,2-d]pyrimidine and 914 mg (16.0 mmol) of allylamine were heated in a sealed tube at 160° C. for 16 hours. After completion of the reaction, the reaction mixture was allowed to resume room temperature, followed by adding a saturated aqueous sodium hydrogen carbonate solution thereto and extraction with ethyl acetate (50 ml×2). After the organic layer was washed with brine and dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4) to give 274 mg (yield: 81.5%) of the title compound.
Aufarbeitung
- customAfter completion of the reaction
- customto resume room temperature
- extractionextraction with ethyl acetate (50 ml×2)
- washAfter the organic layer was washed with brine
- dry with materialdried over anhydrous sodium sulfate
- distillationthe solvent was distilled off
- customThe residue was purified by silica gel chromatography (eluent: ethyl acetate-hexane=1/4)
Quellen und Nachweise
- ORD-Eintrag
- ord-76c9eb527b8c4ec5afbde221d7773635
- Quelldatensatz
- uspto-grants-2002_01
- Patentnummer
- US06339089B2
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