9-Benzyl-9H-purine → 9-Benzyl-8-bromo-9H-purine

HRID 1297154노트

반응식

HRID 1297154 반응식
[CH2:1]([N:8]1[CH:16]=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Br:17]NC(=O)CCC(N)=O>C(Cl)(Cl)Cl>[CH2:1]([N:8]1[C:16]([Br:17])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][CH:13]=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2347019-Benzyl-9H-purineHCID 9834204N-Bromosuccinamide

생성물 1

HCID 589145899-Benzyl-8-bromo-9H-purine

시약·촉매·용매 1

HCID 6212Chloroform용매

실험 절차

To a stirred solution of 12 (10.68 g, 50.7 mmol) in chloroform (500 mL) was added N-bromosuccinamide (45.20 g, 253.9 mmol) and the reaction mixture stirred under an atmosphere of nitrogen and at reflux temperature for 5 h. The reaction mixture was transferred to a separatory funnel and washed with saturated sodium sulfite solution (2×250 mL) followed by brine solution (2×250 mL). The chloroform fraction was dried over anhydrous sodium sulfate and concentrated and the reddish oil was purified by flash chromatography on silica gel using EtOAc/hexane (4:6) for elution. Yield 6.05 g. (41.2%). Mp 119-121° C.; 1H NMR (CDCl3): δ 5.53 (s, 2H, CH2), 7.35-7.39 (m, 5H, Ar—H), 9.03 (s, 1H, purine C8—H), 9.09 (s, 1H, purine C2—H).

후처리

  1. temperatureat reflux temperature for 5 h
  2. customThe reaction mixture was transferred to a separatory funnel
  3. washwashed with saturated sodium sulfite solution (2×250 mL)
  4. dry with materialThe chloroform fraction was dried over anhydrous sodium sulfate
  5. concentrationconcentrated
  6. customthe reddish oil was purified by flash chromatography on silica gel
  7. washfor elution

출처 및 근거

ORD 기록
ord-dd57689fbb8343d591ef0c3e6323f6e5
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250421B2

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