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

HRID 410162ノート

反応式

HRID 410162 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-1bc1870b1aa743c6aa37a583f894f1ff
出典データセット
uspto-grants-2014_06
特許番号
US08759532B2

反応ノート

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