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

HRID 516170ノート

反応式

HRID 516170 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-73f1a10a60b04d069e5bc04a234c6324
出典データセット
uspto-grants-2015_08
特許番号
US09108973B2

反応ノート

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