Reaktion #69286

Reaktionsgleichung

4-[1-(1-cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)-ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

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product

Ausbeute 81.9%

4-[1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7H-pyrrolo[2,3-d]pyrimidine

Ausbeute 81.9%

Lösungsmittel

DCM

TFA

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvents were removed in vacuo
2. 2
   workup.DISSOLUTIONThe resulting residue was dissolved in THF (3 mL)
3. 3
   workup.ADDITION6N NaOH (2 mL) was added
4. 4
   Sonstigethe mixture was partitioned between water and ethyl acetate
5. 5
   TrocknenThe organic layer was dried over sodium sulfate
6. 6
   Sonstigethe solvent was removed in vacuo
7. 7
   SonstigePurification via preparative-HPLC/MS (C18
8. 8
   Wascheneluting with a gradient of H2O and ACN containing 0.1% TFA)

Vorschrift

A solution of 4-[1-(1-cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)-ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine (52 mg, 0.12 mmol) in DCM (3 mL) and TFA (1 mL) was stirred for 2 hours. The solvents were removed in vacuo. The resulting residue was dissolved in THF (3 mL) and 6N NaOH (2 mL) was added. After stirring for 1 hour, the mixture was partitioned between water and ethyl acetate. The organic layer was dried over sodium sulfate and the solvent was removed in vacuo. Purification via preparative-HPLC/MS (C18 eluting with a gradient of H2O and ACN containing 0.1% TFA) afforded product (30 mg, 60%).

Quelle