Reaktionsgleichung
[OH:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[C:9]([O-:12])([O-])=O.[K+].[K+].Cl[C:16]1[CH:21]=[N:20][CH:19]=[C:18]([NH:22][C:23]2[CH:28]=[C:27](OC)[C:26]([O:31][CH3:32])=[C:25]([O:33][CH3:34])[CH:24]=2)[N:17]=1.[CH3:35]N(C)C=O>>[CH3:32][O:31][C:26]1[CH:27]=[C:28]([CH:35]=[C:24]([O:12][CH3:9])[C:25]=1[O:33][CH3:34])[CH2:23][NH:22][C:18]1[CH:19]=[N:20][CH:21]=[C:16]([O:1][C:2]2[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=2)[N:17]=1Komponenten
Versuchsvorschrift
Method CC. To 58.0 mg (0.53 mmol) 4-hydroxyaniline, in 5 mL dimethylformamide were added under stirring and argon 67 mg (0.60 mmol) K-tert-BuO and 42 mg (0.3 mmol) K2CO3. After 5 minutes, 150 mg (0.51 mmol) 2-chloro-6-(3,4,5-trimethoxyphenylamino)-pyrazine were added and the reaction mixture submitted to microwave (30 minutes, 110° C., 200 W). The reaction mixture was filtered and poured in 20 mL water. The emulsion was extracted with (2×20 mL) AcOEt, the organic layer pooled, dried and evaporated to a volume of 2-3 mL. After purification by flash chromatography (Isolute column, Flash Sill, 50 g, 150 mL; eluent; AcOEt), 48.9 mg (26.0%) of the title compound were obtained. 1H-NMR (DMSO), δ (ppm), J (Hz): 3.59 (s, 12H, CH3O3′+4+5′), 6.68 (d, 2H, Harom 3″+5″, J=8.42), 6.87 (s, 2H, Harom 2′+6′), 7.32 (d, 2H, Harom 2″+6″), 7.43 (s, 2H, HP3+5), 8.75 (s, 2H, NHamino), 8.96 (s, 2H, NHamino), 9.07 (s, 2H, OHphenol); MS, (C19H20N4O4), m/z: 369.1 [M++1], 100.
Aufarbeitung
- custom(30 minutes, 110° C., 200 W)
- filtrationThe reaction mixture was filtered
- additionpoured in 20 mL water
- extractionThe emulsion was extracted with (2×20 mL) AcOEt
- customdried
- customevaporated to a volume of 2-3 mL
- customAfter purification by flash chromatography (Isolute column, Flash Sill, 50 g, 150 mL; eluent; AcOEt)
Quellen und Nachweise
- ORD-Eintrag
- ord-9028290e8c7c47088f6658b7ceb1b743
- Quelldatensatz
- uspto-grants-2010_06
- Patentnummer
- US07737152B2
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