反应 #554677

反应方程式

TFA

tert-butyl N-tert-butoxycarbonyl-N-[3-ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate

→

title product

收率 93.2%

3-Ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine

收率 93.2%

溶剂

DCM

反应条件

后处理

1. 1
   其他The solvent was removed in vacuo
2. 2
   workup.DISSOLUTIONthe residue re-dissolved in DCM
3. 3
   workup.STIRRINGstirred with saturated aqueous NaHCO3 for 30 minutes
4. 4
   其他The layers were separated
5. 5
   洗涤the organic layer washed with saturated aqueous NaHCO3 (×3)
6. 6
   萃取The combined aqueous layers were extracted with DCM (×3)
7. 7
   干燥the combined organic extracts dried (MgSO4)
8. 8
   过滤filtered
9. 9
   浓缩concentrated in vacuo
10. 10
    其他The residue was triturated from DCM
11. 11
    其他precipitate
12. 12
    其他isolated by filtration
13. 13
    其他dried under vacuum

实验过程

TFA (34.45 g, 23.28 mL, 302.1 mmol) was added to a stirred solution of tert-butyl N-tert-butoxycarbonyl-N-[3-ethynyl-5-(4-isopropylsulfonylphenyl)pyrazin-2-yl]carbamate (5 g, 9.968 mmol) in DCM (200 mL) and the reaction mixture stirred at ambient temperature for 1.5 hours. The solvent was removed in vacuo and the residue re-dissolved in DCM and stirred with saturated aqueous NaHCO3 for 30 minutes. The layers were separated and the organic layer washed with saturated aqueous NaHCO3 (×3). The combined aqueous layers were extracted with DCM (×3) and the combined organic extracts dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from DCM and precipitate isolated by filtration and dried under vacuum to give the title product as a beige solid (2.8 g, 93% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.18 (d, 6H), 3.44 (t, 1H), 4.76 (s, 1H), 7.01 (s, 2H), 7.89 (d, 2H), 8.20 (d, 2H) and 8.75 (s, 1H) ppm; MS (ES+) 302.12.

来源