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

HRID 1270259
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HRID 1270259 반응식
[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
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참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a5a880ab2ae5481081e2f67ea1970a01
출처 데이터셋
uspto-grants-2007_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07202224B2

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