반응 #73214

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3-cyclopentylidene-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

→

desired product

수율 33.3%

3-Cyclopentylidene-3-[4-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile

수율 33.3%

용매

DCM

TFA

반응 조건

후처리

1. 1
   기타The solvents were evaporated in vacuo
2. 2
   workup.ADDITIONThe reaction mixture was neutralized by dropwise addition of concentrated HCl
3. 3
   추출The product was extracted with ethyl acetate
4. 4
   건조The combined organic extracts were dried over sodium sulfate
5. 5
   여과filtered
6. 6
   농축concentrated in vacuo
7. 7
   기타The crude residue was purified by preparative-HPLC/MS (C18 column
8. 8
   세척eluting with a gradient of ACN/H2O containing 0.15% NH4OH)

실험 절차

A solution of 3-cyclopentylidene-3-[4-(7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]-pyrimidin-4-yl)-1H-pyrazol-1-yl]propanenitrile (0.030 g, 0.069 mmol) in DCM (3 mL) and TFA (2 mL) was stirred for 1 hour. The solvents were evaporated in vacuo and the product was stirred with sodium hydroxide, 50% aqueous solution (0.75 mL) and water (0.75 mL) and THF (1.5 mL) for 2 hours. The reaction mixture was neutralized by dropwise addition of concentrated HCl. The product was extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude residue was purified by preparative-HPLC/MS (C18 column eluting with a gradient of ACN/H2O containing 0.15% NH4OH) to afford the desired product (7 mg, 33%).

출처