반응 #44552

반응 방정식

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

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

3,4,5-trimethoxyaniline

sodium tert-butoxide

→

title compound

수율 17.0%

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

수율 17.0%

용매

toluene

반응 조건

후처리

1. 1
   기타In a tube suitable for microwave irradiation
2. 2
   기타provided
3. 3
   기타The reaction crude
4. 4
   여과was filtered
5. 5
   세척the precipitate washed with boiling ethyl acetate (30 mL)
6. 6
   기타The organic layers were evaporated under vacuum
7. 7
   기타the resulting crude was chromatographed
8. 8
   workup.ADDITION(eluent: mixture of ethyl acetate and methanol; 9:1)

실험 절차

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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