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

HRID 41008Notes

Reaction equation

HRID 41008 reaction equation
[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][N:21](COCC[Si](C)(C)C)[C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[CH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:1]1([CH:6]([N:10]2[CH:14]=[C:13]([C:15]3[C:16]4[CH:23]=[CH:22][NH:21][C:17]=4[N:18]=[CH:19][N:20]=3)[CH:12]=[N:11]2)[CH2:7][C:8]#[CH:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 574781104-[1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl]-7-[2-(trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidine

Product 1

HCID 574780084-(1-(1-Cyclopentylbut-3-yn-1-yl)-1H-pyrazol-4-yl)-7H-pyrrolo[2,3-d]pyrimidineYield 81.9%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

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%).

Workup

  1. customThe solvents were removed in vacuo
  2. dissolutionThe resulting residue was dissolved in THF (3 mL)
  3. addition6N NaOH (2 mL) was added
  4. customthe mixture was partitioned between water and ethyl acetate
  5. dry with materialThe organic layer was dried over sodium sulfate
  6. customthe solvent was removed in vacuo
  7. customPurification via preparative-HPLC/MS (C18
  8. washeluting with a gradient of H2O and ACN containing 0.1% TFA)

Sources & evidence

ORD record
ord-30c27854323b4bbba2e87365642d5cfc
Source dataset
uspto-grants-2013_09
Patent number
US08530485B2

Reaction notes

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