Potassium Carbonate → 3-ethyl-1-(3-hydroxypropyl)-7-((6-methylpyridin-3-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

HRID 2200687ノート

反応式

HRID 2200687 の反応式
[CH2:1]([N:3]1[C:11]2[N:10]=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:23])([F:22])[F:21])[CH:14]=3)[NH:8][C:7]=2[C:6](=[O:24])[N:5]([CH2:25][CH2:26][CH2:27][OH:28])[C:4]1=[O:29])[CH3:2].Cl[CH2:31][C:32]1[CH:33]=[CH:34][C:35]([CH3:38])=[N:36][CH:37]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[CH2:1]([N:3]1[C:11]2[N:10]=[C:9]([O:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:20]([F:22])([F:23])[F:21])[CH:14]=3)[N:8]([CH2:31][C:32]3[CH:37]=[N:36][C:35]([CH3:38])=[CH:34][CH:33]=3)[C:7]=2[C:6](=[O:24])[N:5]([CH2:25][CH2:26][CH2:27][OH:28])[C:4]1=[O:29])[CH3:2]

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 122143385-(Chloromethyl)-2-methylpyridineHCID 904027233-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione

生成物 1

HCID 904024753-ethyl-1-(3-hydroxypropyl)-7-((6-methylpyridin-3-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione収率 44.8%

試薬・触媒・溶媒 2

HCID 67553Tetrabutylammonium Iodide触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3-ethyl-1-(3-hydroxypropyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (110 mg, 0.22 mmol) in DMF (3 mL) was added 5-(chloromethyl)-2-methylpyridine (50 mg, 0.4 mmol), potassium carbonate (91 mg, 0.66 mmol), and TBAI (2 mg, 0.02 mmol). The reaction was heated at 50° C. overnight. The mixture was cooled and partitioned between ethyl acetate and water. The combined organic layer was dried over sodium sulfate, filtered and concentrated to give a crude product, which was purified by preparative HPLC to give 3-ethyl-1-(3-hydroxypropyl)-7-((6-methylpyridin-3-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dione (30 mg, 44.8% yield) as a white solid.

後処理

  1. temperatureThe mixture was cooled
  2. custompartitioned between ethyl acetate and water
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product, which
  7. customwas purified by preparative HPLC

出典と根拠

ORDレコード
ord-07fbdbbde0bb42cfa69405fa25642e4a
出典データセット
uspto-grants-2016_06
特許番号
US09359359B2

反応ノート

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