تفاعل #73214

معادلة التفاعل

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

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desired product

المردود 33.3%

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

المردود 33.3%

المذيبات

DCM

TFA

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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%).

المصدر