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Trifluoroacetic acid → 5-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1692842
ノート
印刷プレビュー

反応式

HRID 1692842 の反応式
[CH3:1][S:2][C:3]1[N:8]=[CH:7][C:6]([CH:9]([C:11]2[C:19]3[CH:18]=[N:17][CH:16]=[N:15][C:14]=3[N:13]([Si](C(C)C)(C(C)C)C(C)C)[CH:12]=2)O)=[CH:5][N:4]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCCl>[CH3:1][S:2][C:3]1[N:4]=[CH:5][C:6]([CH2:9][C:11]2[C:19]3[CH:18]=[N:17][CH:16]=[N:15][C:14]=3[NH:13][CH:12]=2)=[CH:7][N:8]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 57963217(2-methylsulfanyl-pyrimidin-5-yl)-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol

生成物 1

HCID 579631715-(2-methylsulfanyl-pyrimidin-5-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidine収率 72.9%

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
80 °C

実験手順

To a solution of (2-methylsulfanyl-pyrimidin-5-yl)-(7-triisopropylsilanyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-methanol (55, 2.75 g, 6.40 mmol) in 50.0 mL of 1,2-dichloroethane, triethylsilane (8.00 mL, 50.1 mmol) and trifluoroacetic acid (4.00 mL, 51.9 mmol) were added. The reaction was heated at 80° C. overnight, then concentrated under vacuum, combined with water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered, and the filtrate was concentrated under vacuum. The resulting material was purified by silica gel column chromatography eluting with 2-15% methanol in dichloromethane. Appropriate fractions were combined and the solvents removed under vacuum to provide the desired compound (56, 1.20 g). MS (ESI) [M+H+]+=258.2.

後処理

  1. concentrationconcentrated under vacuum
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under vacuum
  6. customThe resulting material was purified by silica gel column chromatography
  7. washeluting with 2-15% methanol in dichloromethane
  8. customthe solvents removed under vacuum

出典と根拠

ORDレコード
ord-f8eb45e78ab342d49284d6e8eb5b6772
出典データセット
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08158636B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート