Potassium Carbonate → 8-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine

HRID 1011033ノート

反応式

HRID 1011033 の反応式
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10]1[NH:11][C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[N:13]=2.C(=O)([O-])[O-].[K+].[K+].CS(O[CH2:38][CH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)(=O)=O>CN(C=O)C>[CH3:8][O:9][C:10]1[N:11]([CH2:38][CH:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[C:12]2[C:17]([N:18]=1)=[C:16]([NH2:19])[N:15]=[C:14]([O:20][CH2:21][CH:22]1[CH2:26][CH2:25][CH2:24][O:23]1)[N:13]=2

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 15166436Oxan-4-ylmethyl methanesulfonateHCID 178493992HCID 178493992、化合物

生成物 1

HCID 576996338-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9-(tetrahydro-2H-Pyran-4-ylmethyl)-9H-purin-6-amine収率 54.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

8-(Methoxy)-2-[(tetrahydro-2-furanylmethyl)oxy]-9H-purin-6-amine trifluoroacetate salt (0.30 g) was dissolved in dry DMF (5 mL). To this solution was added anhydrous potassium carbonate (0.4376 g) and then the reaction mixture was heated to 60° C. under nitrogen for 1 hour. The reaction mixture was then cooled to room temperature before adding tetrahydro-2H-pyran-4-ylmethyl methanesulfonate (0.1690 g) and then the resultant reaction mixture was heated to 90° C. for 2.5 hours. The reaction mixture was cooled and then quenched with water (50 mL), followed by extraction into ethyl acetate (50 mL, 3 times). After separating, the organic layers were combined and dried by passing through a hydrophobic frit. Evaporation under reduced pressure gave mobile oil which was then purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (10-45%). This gave the title compound as a white solid (0.1560 g).

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. customthe resultant reaction mixture
  3. temperaturewas heated to 90° C. for 2.5 hours
  4. temperatureThe reaction mixture was cooled
  5. customquenched with water (50 mL)
  6. extractionfollowed by extraction into ethyl acetate (50 mL, 3 times)
  7. customAfter separating
  8. customdried
  9. customEvaporation under reduced pressure
  10. customgave mobile oil which
  11. customwas then purified by C18 reverse phase chromatography

出典と根拠

ORDレコード
ord-467e74118f194d50af7659e42162595c
出典データセット
uspto-grants-2011_07
特許番号
US07977344B2

反応ノート

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