Tetrahydrofuran → HCID 68513914, Verbindung

HRID 2241223Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2241223
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([CH2:7][N:8]2[C:12]3=[N:13][CH:14]=[CH:15][C:16](Cl)=[C:11]3[C:10]([CH3:18])=[N:9]2)=[CH:5][CH:4]=1.[Cl:21][C:22]1[CH:43]=[CH:42][C:25]([CH2:26][N:27]2[C:32](=[O:33])[C:31]([C:34]3[CH:39]=[CH:38][C:37]([OH:40])=[C:36]([F:41])[CH:35]=3)=[CH:30][N:29]=[CH:28]2)=[CH:24][CH:23]=1.CC(C)([O-])C.[K+].C1COCC1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:21][C:22]1[CH:23]=[CH:24][C:25]([CH2:26][N:27]2[C:32](=[O:33])[C:31]([C:34]3[CH:39]=[CH:38][C:37]([O:40][C:16]4[CH:15]=[CH:14][N:13]=[C:12]5[N:8]([CH2:7][C:6]6[CH:19]=[CH:20][C:3]([O:2][CH3:1])=[CH:4][CH:5]=6)[N:9]=[C:10]([CH3:18])[C:11]=45)=[C:36]([F:41])[CH:35]=3)=[CH:30][N:29]=[CH:28]2)=[CH:42][CH:43]=1

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 23665647Potassium tert-butoxideHCID 685123991-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridineHCID 68516482HCID 68516482, Verbindung

Produkt 1

HCID 68513914HCID 68513914, VerbindungAusbeute 137,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

To a 10 mL round bottom flask was added 1-(4-methoxybenzyl)-4-chloro-3-methyl-1H-pyrazolo[3,4-b]pyridine (13.0 mg, 0.0454 mmol), prepared according to the procedure of Example 43, Step E, 3-(4-chlorobenzyl)-5-(3-fluoro-4-hydroxyphenyl)pyrimidin-4(3H)-one (10 mg, 0.0302 mmol) prepared according to the procedure of Example 43, Step D and dissolved in DMF (0.5 mL). A 1M solution of potassium t-butoxide in THF (0.0454 mL, 0.0454 mmol) and potassium carbonate (6.27 mg, 0.0454 mmol) were both added and the resulting mixture was stirred at 110° C. for 3 hours. The reaction mixture was cooled to room temperature and the crude mixture was partitioned between water (10 mL) and ethyl acetate (15 mL). The organic layer washed with brine, dried over sodium sulfate and evaporated to afford 24.1 mg of brown oil. The crude product was purified by silica gel chromatography (Biotage 12M), loading with chloroform and eluting with 1.5% MeOH in CHCl3 to afford the desired product as an off-white solid (5 mg, 28%). LRMS (APCI pos) m/e 583.2 (M+1).

Aufarbeitung

  1. customprepared
  2. customprepared
  3. additionboth added
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customthe crude mixture was partitioned between water (10 mL) and ethyl acetate (15 mL)
  6. washThe organic layer washed with brine
  7. dry with materialdried over sodium sulfate
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-9347a7482b1d4394969bd320d1213a1f
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723330B2

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