3,4-dihydro-2H-pyran → 6-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

HRID 410162노트

반응식

HRID 410162 반응식
[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[O:11]1[CH:16]=[CH:15][CH2:14][CH2:13][CH2:12]1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CCOC(C)=O>[Br:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:12]1[CH2:13][CH2:14][CH2:15][CH2:16][O:11]1

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 5287830Purine, 6-bromo-

생성물 1

HCID 583686166-Bromo-9-(tetrahydro-2H-pyran-2-YL)-9H-purine

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6-bromopurine (2.0 g, 10 mmol), 3,4-dihydro-2h-pyran (1.0 ml, 11 mmol), and p-toluenesulfonic acid monohydrate (0.050 g, 0.26 mmol) in EtOAc (30 mL) was stirred at reflux under a reflux condenser for 48 h. The reaction mixture (suspension) was allowed to cool to room temperature and the solid was removed by suction filtration and washed with EtOAc (50 mL). The combined wash was concentrated in vacuo to afford 2.1 g as oil. The oil was chromatographed through a Redi-Sep® pre-packed silica gel column, eluting with a gradient of 30% to 60% EtOAc in hexane, to provide product.

후처리

  1. temperatureat reflux under a reflux condenser for 48 h
  2. customthe solid was removed by suction filtration
  3. washwashed with EtOAc (50 mL)
  4. washThe combined wash
  5. concentrationwas concentrated in vacuo
  6. customto afford 2.1 g as oil
  7. customThe oil was chromatographed through a Redi-Sep® pre-packed silica gel column
  8. washeluting with a gradient of 30% to 60% EtOAc in hexane
  9. customto provide product

출처 및 근거

ORD 기록
ord-1bc1870b1aa743c6aa37a583f894f1ff
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

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