Trifluoroacetic acid → 5-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

HRID 516170Notes

Reaction equation

HRID 516170 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[C:21]3[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=3[N:15](COCC[Si](C)(C)C)[CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]#[C:12][C:13]2[C:21]3[C:20]([NH2:22])=[N:19][CH:18]=[N:17][C:16]=3[NH:15][CH:14]=2)[CH:6]=[C:7]([O:9][CH3:10])[CH:8]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 898710195-((3,5-dimethoxyphenyl)ethynyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine

Product 1

HCID 898708605-((3,5-dimethoxyphenyl)ethynyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amineYield 87.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-((3,5-dimethoxyphenyl)ethynyl)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (4.27 g) obtained in Step 3 in methylene chloride (20 ml) was cooled to 0° C., and TFA 10 ml was added thereto. The reaction mixture was stirred at room temperature for 5 hours, and the solvent was distilled off under reduced pressure. THF (50 ml) was added to the residue, and the mixture was cooled to 0° C. 4N aqueous sodium hydroxide (12.5 ml) was added thereto, and the mixture was stirred at room temperature overnight. The result was extracted with ethyl acetate, and dried over anhydrous magnesium sulfate. Subsequently, the solvent was distilled off under reduced pressure, and chloroform was added to the resulting residue. The mixture was subjected to filtration to obtain the title compound as a white solid (2.60 g). Physical properties: m/z [M+H]+ 295.3

Workup

  1. distillationthe solvent was distilled off under reduced pressure
  2. additionTHF (50 ml) was added to the residue
  3. temperaturethe mixture was cooled to 0° C
  4. addition4N aqueous sodium hydroxide (12.5 ml) was added
  5. stirringthe mixture was stirred at room temperature overnight
  6. extractionThe result was extracted with ethyl acetate
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationSubsequently, the solvent was distilled off under reduced pressure, and chloroform
  9. additionwas added to the resulting residue
  10. filtrationThe mixture was subjected to filtration

Sources & evidence

ORD record
ord-73f1a10a60b04d069e5bc04a234c6324
Source dataset
uspto-grants-2015_08
Patent number
US09108973B2

Reaction notes

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