Potassium Carbonate → HCID 90402626, Verbindung

HRID 2200707Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200707
[CH3:1][N:2]1[C:10]2[N:9]=[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:6]=2[C:5](=[O:31])[NH:4][C:3]1=[O:32].[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36]OS(C1C=CC(C)=CC=1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[OH:33][CH:34]([CH3:48])[CH2:35][CH2:36][N:4]1[C:5](=[O:31])[C:6]2[N:7]([CH2:23][C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][N:25]=3)[C:8]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][C:19]([F:22])([F:21])[F:20])[CH:13]=3)=[N:9][C:10]=2[N:2]([CH3:1])[C:3]1=[O:32]

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 132043233-Hydroxybutyl 4-methylbenzenesulfonateHCID 90402690HCID 90402690, Verbindung2×

Produkt 1

HCID 90402626HCID 90402626, VerbindungAusbeute 26 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of 3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (30 mg, 0.067 mmol, intermediate 51) in DMF (3 mL) was added 3-hydroxybutyl-4-methylbenzenesulfonate (24.68 mg, 0.10 mmol), followed by potassium carbonate (27.93 mg, 0.20 mmol). The reaction was stirred at 70° C. for 4 h. The mixture was partitioned between ethyl acetate and water. The organic phase was washed with brine, dried over sodium sulfate, filtered and concentrated to give crude product, which was purified by preparative HPLC to give 1-(3-hydroxybutyl)-3-methyl-7-((5-methylpyridin-2-yl)methyl)-8-(3-(trifluoromethoxy)benzyl)-1H-purine-2,6(3H,7H)-dione (9 mg, 25.8%) as white solid. 1H-NMR (CD3OD) δ 8.216(s,1H), 7.491-7.467(d,1H), 7.312-7.272(m,1H), 7.154-6.995(m,4H), 5.688(s,2H), 4.305(s,2H), 4.143-4.011(m,2H), 3.772-3.440(m,1H), 3.585(s, 3H), 2.283(s,3H), 1.761-1.703(m,2H), 1.194-1.179(d,3H). LCMS retention time 2.569 min; LCMS MH+ 518.

Aufarbeitung

  1. customThe mixture was partitioned between ethyl acetate and water
  2. washThe organic phase was washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give crude product, which
  7. customwas purified by preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-4ab2429b57f44f769d9412966fb6c234
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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