Potassium Carbonate → N2-Butyl-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine

HRID 1010931ノート

反応式

HRID 1010931 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][CH:33]1[CH2:38][CH2:37][CH2:36][O:35][CH2:34]1>CN(C)C=O.C(OCC)(=O)C>[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][CH:33]2[CH2:38][CH2:37][CH2:36][O:35][CH2:34]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 226172573-(Bromomethyl)oxaneHCID 178448879HCID 178448879、化合物

生成物 1

HCID 57699736N2-Butyl-8-methoxy-9-(tetrahydro-2H-pyran-3-ylmethyl)-9H-purine-2,6-diamine収率 47.1%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

To a solution of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (100 mg) in dry N,N-dimethylformamide (1 ml) at room temperature and under nitrogen was added potassium carbonate (158 mg) in one go. The reaction was stirred at 60° C. for 1.5 hours and then cooled to 50° C. A solution of 3-(bromomethyl)tetrahydro-2H-pyran (56 mg) in dry N,N-dimethylformamide (0.3 ml) was added in one go and the reaction heated at 50° C. for 16 hours. The reaction was diluted with ethyl acetate (15 ml) and washed with water (5 ml). The organic layer was separated, dried over magnesium sulphate, filtered, and concentrated in vacuo. The product was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluant (20-60%) to afford the title compound as a yellow oil (45 mg).

後処理

  1. temperaturecooled to 50° C
  2. temperaturethe reaction heated at 50° C. for 16 hours
  3. washwashed with water (5 ml)
  4. customThe organic layer was separated
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by C18 reverse phase chromatography

出典と根拠

ORDレコード
ord-6cb6283218744de98923256f06e5521f
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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