Reaktion #44553

Reaktionsgleichung

4-hydroxyaniline

dimethylformamide

K2CO3

2-chloro-6-(3,4,5-trimethoxyphenylamino)-pyrazine

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title compound

Ausbeute 26.0%

2-(3,4,5-trimethoxybenzylamino)-6-(4-aminophenyloxy)-pyrazine

Ausbeute 26.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstige(30 minutes, 110° C., 200 W)
2. 2
   FiltrationThe reaction mixture was filtered
3. 3
   workup.ADDITIONpoured in 20 mL water
4. 4
   ExtraktionThe emulsion was extracted with (2×20 mL) AcOEt
5. 5
   Sonstigedried
6. 6
   Sonstigeevaporated to a volume of 2-3 mL
7. 7
   SonstigeAfter purification by flash chromatography (Isolute column, Flash Sill, 50 g, 150 mL; eluent; AcOEt)

Vorschrift

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.

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