반응 #428416

반응 방정식

O-(Mesitylenesulfonyl)hydroxylamine

2-bromo-5-trimethylsilanylethynyl-pyrazine

2-Bromo-5-trimethylsilanylethynyl-pyrazine

K2CO3

N-aminopyrazine

→

title compound

수율 7.6%

6-Bromo-2-trimethylsilanyl-pyrazolo[1,5-a]pyrazine

수율 7.6%

용매

CH2Cl2

DMF

반응 조건

후처리

1. 1
   기타evaporated
2. 2
   기타After 6 hours the mixture was partitioned between EtOAc/H2O
3. 3
   세척The organic layer was washed with brine (×2)
4. 4
   기타evaporated
5. 5
   기타separating cartridge
6. 6
   기타The filtrate was evaporated
7. 7
   기타the residue was purified by chromatography on silica (2→4% EtOAc/Petrol)

실험 절차

O-(Mesitylenesulfonyl)hydroxylamine (680 mg, 3.2 mmol) was added in one portion to a stirred solution of 2-bromo-5-trimethylsilanylethynyl-pyrazine (Step 1, 3 mmol) in CH2Cl2 (3 ml) at 0° C. The mixture was stirred at 0° C. for 30 minutes, at RT for 4 hours, then evaporated. The N-amino adduct was used without further manipulation. K2CO3 (410 mg, 3 mmol) was added to a stirred solution of the N-aminopyrazine from above in dry DMF (5 ml) at RT under nitrogen. After 6 hours the mixture was partitioned between EtOAc/H2O. The organic layer was washed with brine (×2), then evaporated. The residue was taken up in CH2Cl2 and passed through a phase separating cartridge. The filtrate was evaporated and the residue was purified by chromatography on silica (2→4% EtOAc/Petrol) to give the title compound (62 mg, oil) MS: [M+H]+ 270/272.

출처