반응 #68931

반응 방정식

TsOH

2-amino-5-cyanopyrazine

sodium tert-butoxide

N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine

→

title compound

수율 73.5%

5-(4-(4-Methoxybenzylamino)-5-nitropyridin-2-ylamino)pyrazine-2-carbonitrile

수율 73.5%

용매

DMF

toluene

반응 조건

후처리

1. 1
   기타was degassed under a stream of nitrogen gas
2. 2
   기타the mixture was degassed for a further 5 minutes
3. 3
   온도Upon cooling
4. 4
   workup.ADDITIONthe mixture was diluted with methanol
5. 5
   기타isolated by SPE
6. 6
   세척washing with methanol
7. 7
   세척eluting with 2 M ammonia in methanol
8. 8
   농축The basic fractions were concentrated in vacuo

실험 절차

A mixture of palladium (II) acetate (38 mg, 0.17 mmol) and (±)-2,2″-bis(diphenylphosphino)-1,1″-binaphthalene (318 mg, 0.51 mmol) a mixture of toluene and DMF (1:1, 10 mL) was degassed under a stream of nitrogen gas with stirring for 30 minutes. After addition of 2-amino-5-cyanopyrazine (245 mg, 2.04 mmol), sodium tert-butoxide (196 mg, 2.04 mmol) and N-(4-methoxybenzyl)-2-bromo-5-nitropyridin-4-amine (575 mg, 1.70 mmol), the mixture was degassed for a further 5 minutes and then heated at 140° C. for 30 minutes in a microwave reactor. Upon cooling, the mixture was diluted with methanol and isolated by SPE using 3×2.5 g MP-TsOH cartridges, washing with methanol and then eluting with 2 M ammonia in methanol. The basic fractions were concentrated in vacuo to give the title compound (470 mg, 1.25 mmol, 73%) which was used without further purification. LCMS (2) Rt=2.18 min; m/z (ESI−) 376 (M−H); (ESI+) 378 (MH+).

출처