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Boron Trichloride → 4-Chloro-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 1270259
ノート
印刷プレビュー

反応式

HRID 1270259 の反応式
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][O:28]CC4C=CC(Cl)=CC=4Cl)[C@@H:14]([O:15]CC4C=CC(Cl)=CC=4Cl)[C@@:12]3([CH2:38][CH3:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=1.B(Cl)(Cl)Cl>ClCCl>[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([C@@H:11]3[O:26][C@H:25]([CH2:27][OH:28])[C@@H:14]([OH:15])[C@@:12]3([CH2:38][CH3:39])[OH:13])[C:4]=2[N:5]=[CH:6][N:7]=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

4

反応物 2

HCID 25135Boron TrichlorideHCID 872855044-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-ethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

生成物 1

HCID 865860784-Chloro-7-(2-C-ethyl-beta-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidine収率 79.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of the compound from Step B (307 mg, 0.45 mmol) in dichloromethane (8 mL) was added boron trichloride (1M in dichloromethane) (4.50 mL, 4.50 mmol) at −78° C. The mixture was stirred at −78° C. for 1 h, then at −10° C. for 3 h. The reaction was quenched by addition of methanol/dichloromethane (1:1) (10 mL), stirred at −15° C. for 30 min, and neutralized by addition of aqueous ammonium hydroxide. The mixture was evaporated in vacuo and the resulting oil purified on silica gel using methanol/dichloromethane (1:9) as eluent. Fractions containing the product were pooled and evaporated in vacuo to give the desired product (112 mg) as a colorless foam.

後処理

  1. waitat −10° C. for 3 h
  2. customThe reaction was quenched by addition of methanol/dichloromethane (1:1) (10 mL)
  3. stirringstirred at −15° C. for 30 min
  4. additionneutralized by addition of aqueous ammonium hydroxide
  5. customThe mixture was evaporated in vacuo
  6. customthe resulting oil purified on silica gel
  7. additionFractions containing the product
  8. customevaporated in vacuo

出典と根拠

ORDレコード
ord-a5a880ab2ae5481081e2f67ea1970a01
出典データセット
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07202224B2

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