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 2200687Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200687
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 904024753-ethyl-1-(3-hydroxypropyl)-7-((6-methylpyridin-3-yl)methyl)-8-(3-(trifluoromethoxy)phenoxy)-1H-purine-2,6(3H,7H)-dioneAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-07fbdbbde0bb42cfa69405fa25642e4a
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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