Water → N2-Butyl-8-methoxy-9-[2-(tetrahydrofuran-2-yl)ethyl]-9H-Purine-2,6-diamine

HRID 1010938ノート

反応式

HRID 1010938 の反応式
FC(F)(F)C(O)=O.[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH:34]1[CH2:38][CH2:37][CH2:36][O:35]1.O>CN(C)C=O>[CH2:8]([NH:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH:34]2[CH2:38][CH2:37][CH2:36][O:35]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

参加物

6

反応物 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 536918712-(2-Bromoethyl)oxolaneHCID 178448879HCID 178448879、化合物

生成物 1

HCID 57699707N2-Butyl-8-methoxy-9-[2-(tetrahydrofuran-2-yl)ethyl]-9H-Purine-2,6-diamine

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

A stirring mixture of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (200 mg) and potassium carbonate (236 mg) in dry N,N-dimethylformamide (2 ml) was heated with stirring at 60° C. for 1 h. 2-(2-Bromoethyl)tetrahydrofuran (122 mg) was added and the stirring mixture heated at 50° C. for 4 h. After allowing to cool, water was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water then brine, dried by passing through a phase separation cartridge and stripped to give a brown oil. This was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (20-60%) and the appropriate fractions combined and evaporated to remove acetonitrile. The remaining aqueous mixture was made basic with saturated sodium hydrogen carbonate, extracted three times with dichloromethane and the combined extracts dried by passing through a phase separation cartridge then evaporated to afford the title compound, yield 107 mg.

後処理

  1. temperaturewas heated
  2. temperaturethe stirring mixture heated at 50° C. for 4 h
  3. temperatureto cool
  4. extractionthe mixture extracted three times with ethyl acetate
  5. washThe combined extracts were washed with water
  6. dry with materialbrine, dried
  7. customby passing through a phase separation cartridge
  8. customto give a brown oil
  9. customThis was purified by C18 reverse phase chromatography
  10. customevaporated
  11. customto remove acetonitrile
  12. extractionextracted three times with dichloromethane
  13. customthe combined extracts dried
  14. customby passing through a phase separation cartridge
  15. customthen evaporated

出典と根拠

ORDレコード
ord-e8170ffc71b04f94a7fb086f575bd606
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

読み込み中…