Реакция #44552

Уравнение реакции

4,5-bis(diphenylphosphino)-9,9-dimethylxanthene

2-bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine

3,4,5-trimethoxyaniline

sodium tert-butoxide

→

title compound

Выход 17.0%

2-(3,4,5-Trimethoxyphenylamino)-3-acetamido-6-(3-acetamidophenyl)pyrazine

Выход 17.0%

Растворители

toluene

Условия реакции

Обработка

1. 1
   ДругоеIn a tube suitable for microwave irradiation
2. 2
   Другоеprovided
3. 3
   ДругоеThe reaction crude
4. 4
   Фильтрацияwas filtered
5. 5
   Промывкаthe precipitate washed with boiling ethyl acetate (30 mL)
6. 6
   ДругоеThe organic layers were evaporated under vacuum
7. 7
   Другоеthe resulting crude was chromatographed
8. 8
   workup.ADDITION(eluent: mixture of ethyl acetate and methanol; 9:1)

Методика

Method AA. In a tube suitable for microwave irradiation provided with stirring and an argon atmosphere were placed 2-bromo-3-acetamido-6-(3-acetamidophenyl)pyrazine (32 mg, 0.09164 mmol), 3,4,5-trimethoxyaniline (33.6 mg, 0.1833 mmol), sodium tert-butoxide (18 mg, 0.1833 mmol), Pd(0)2 dba3 (8.4 mg, 9.164 μmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xant phos) (5.3 mg, 9.164 μmol) and dry toluene 1.5 mL). The tube was heated by microwave irradiation at 110° C. for 30 minutes. The reaction crude was filtered and the precipitate washed with boiling ethyl acetate (30 mL). The organic layers were evaporated under vacuum and the resulting crude was chromatographed (eluent: mixture of ethyl acetate and methanol; 9:1) to produce 7 mg of title compound. Yield: 17%. 1H NMR (250 MHz, DMSO-d6) δ 2.06 (s, 3H), 2.17 (s, 3H), 3.64 (s, 3H), 3.77 (s, 9H), 7.24 (s, 2H), 7.42 (t, 1H, J=8.0 Hz), 7.64 (d, 1H, J=7.7 Hz), 7.73 (d, 1H, J=7.9 Hz), 8.22 (bs, 1H), 8.28 (s, 1H), 8.52 (s, 1H), 10.07 (s, 1H), 10.21 (s, 1H). m/z 452.2 [(M+H)+ calcd for C23H25N5O5 451.2].

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