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 2200687노트

반응식

HRID 2200687 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 67553Tetrabutylammonium Iodide촉매HCID 6228Dimethylformamide용매

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온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-07fbdbbde0bb42cfa69405fa25642e4a
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09359359B2

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