Potassium Carbonate → 2-[(2-Cyclopropylethyl)oxy]-8-(methyloxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine

HRID 1011016ノート

反応式

HRID 1011016 の反応式
FC(F)(F)C(O)=O.[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[NH:20]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH:34]1[CH2:39][CH2:38][O:37][CH2:36][CH2:35]1>CN(C=O)C>[CH:8]1([CH2:11][CH2:12][O:13][C:14]2[N:22]=[C:21]3[C:17]([N:18]=[C:19]([O:23][CH3:24])[N:20]3[CH2:33][CH:34]3[CH2:39][CH2:38][O:37][CH2:36][CH2:35]3)=[C:16]([NH2:25])[N:15]=2)[CH2:10][CH2:9]1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 27732864-(Bromomethyl)oxaneHCID 178493994HCID 178493994、化合物

生成物 1

HCID 576997352-[(2-Cyclopropylethyl)oxy]-8-(methyloxy)-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-Purin-6-amine収率 44.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

反応条件

温度
50 °C

実験手順

2-[(2-Cyclopropylethyl)oxy]-8-methoxy-9H-purin-6-amine trifluoroacetic acid salt (0.30 g) was heated with potassium carbonate (anhydrous, 0.46 g) in anhydrous DMF (5 mL) at 60° C. for 1 hour. The reaction was cooled to room temperature before 4-(bromomethyl) tetrahydro-2H-pyran (0.16 g) in anhydrous DMF (1 mL) was added. The reaction mixture was then heated to 50° C. overnight. The reaction was quenched into water (50 mL) and extracted with ethyl acetate (50 mL, 3 times). The organic layer was combined and washed with brine (50 mL). The organic layer was separated and dried by passing through a hydrophobic frit before being evaporated under reduced pressure to give oil). This material was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (20-60%). This material was purified by reverse phase chromatography (20-60% acetonitrile: water). This gave the title compound as a white solid (0.1279 g).

後処理

  1. additionwas added
  2. customThe reaction was quenched into water (50 mL)
  3. extractionextracted with ethyl acetate (50 mL, 3 times)
  4. washwashed with brine (50 mL)
  5. customThe organic layer was separated
  6. customdried
  7. custombefore being evaporated under reduced pressure
  8. customto give oil)
  9. customThis material was purified by C18 reverse phase chromatography
  10. customThis material was purified by reverse phase chromatography (20-60% acetonitrile: water)

出典と根拠

ORDレコード
ord-6670d8ceb68040b08bc4b3706fe2ee3b
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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