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Hydrogen Bromide → 4-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-ethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine

HRID 1836237
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HRID 1836237 반응식
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][O:10][C@@H:11]1[C@@H:17]([CH2:18][O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=2[Cl:28])[O:16][C@H:13](OC)[C@:12]1([CH2:30][CH3:31])[OH:29].Br.[Cl:33][C:34]1[N:39]=[CH:38][NH:37][C:36]2=[N:40][CH:41]=[CH:42][C:35]=12.[OH-].[K+].COCCOCCN(CCOCCOC)CCOCCOC.[Cl-].[NH4+]>ClCCl.C(#N)C.C(OCC)(=O)C>[Cl:33][C:34]1[C:35]2[CH:42]=[CH:41][N:40]([C@@H:13]3[O:16][C@H:17]([CH2:11][O:10][CH2:9][C:3]4[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=4[Cl:1])[C@@H:18]([O:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])[C@@:12]3([CH2:30][CH3:31])[OH:29])[C:36]=2[N:37]=[CH:38][N:39]=1
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참가 물질

10

반응물 6

HCID 260Hydrogen BromideHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 112414Ethanamine, 2-(2-methoxyethoxy)-N,N-bis[2-(2-methoxyethoxy)ethyl]-HCID 671439003,5-Bis-o-(2,4-dichlorophenylmethyl)-2-c-ethyl-1-o-methyl-alpha-d-ribofuranoseHCID 178418725HCID 178418725, 화합물

생성물 1

HCID 872855044-Chloro-7-[3,5-bis-o-(2,4-dichlorophenylmethyl)-2-c-ethyl-beta-d-ribofuranosyl]-7h-pyrrolo[2,3-d]pyrimidine수율 24.3%

시약·촉매·용매 3

HCID 6342Acetonitrile용매HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

To a solution of the compound from Step A (1.02 mg, 2.0 mmol) in dichloromethane (40 mL) was added HBr (5.7 M in acetic acid) (1.75 mL, 10.0 mmol) dropwise at 0° C. The resulting solution was stirred at rt for 2 h, evaporated in vacuo and co-evaporated twice from toluene (10 mL). The oily residue was dissolved in acetonitrile (10 mL) and added to a vigorously stirred mixture of 4-chloro-1H-pyrrolo[2,3-d]pyrimidine (307 mg, 2.0 mmol), potassium hydroxide (337 mg, 6.0 mmol) and tris[2-(2-methoxyethoxy)ethyl]amine (130 mg, 0.4 mmol) in acetonitrile (10 mL). The resulting mixture was stirred at room temperature overnight, and then poured into a stirred mixture of saturated ammonium chloride (100 mL) and ethyl acetate (100 mL). The organic layer was separated, washed with brine (100 mL), dried over MgSO4, filtered and evaporated in vacuo. The crude product was purified on silica gel using ethyl acetate/hexane (1:2) as eluent to give the desired product (307 mg) as a colorless foam.

후처리

  1. customevaporated in vacuo
  2. dissolutionThe oily residue was dissolved in acetonitrile (10 mL)
  3. stirringThe resulting mixture was stirred at room temperature overnight
  4. customThe organic layer was separated
  5. washwashed with brine (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customThe crude product was purified on silica gel

출처 및 근거

ORD 기록
ord-1c3e91d15d0b43eaadeb93c4924173ca
출처 데이터셋
uspto-grants-2004_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06777395B2

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