Potassium Carbonate → HCID 90402924, Verbindung

HRID 2200705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2200705
[CH3:1][O:2][C:3]1[CH:36]=[CH:35][C:6]([CH2:7][N:8]2[C:16](=[O:17])[C:15]3[NH:14][C:13]([CH2:18][CH2:19][CH2:20][O:21][C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:32])([F:31])[F:30])[CH:23]=4)=[N:12][C:11]=3[N:10]([CH3:33])[C:9]2=[O:34])=[CH:5][CH:4]=1.Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Cl:45])=[CH:41][CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCCC[N+](CCCC)(CCCC)CCCC.[I-]>[Cl:45][C:42]1[CH:43]=[CH:44][C:39]([CH2:38][N:14]2[C:15]3[C:16](=[O:17])[N:8]([CH2:7][C:6]4[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:36][CH:35]=4)[C:9](=[O:34])[N:10]([CH3:33])[C:11]=3[N:12]=[C:13]2[CH2:18][CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:31])([F:32])[F:30])[CH:23]=2)=[CH:40][CH:41]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 90403762HCID 90403762, Verbindung2×

Produkt 1

HCID 90402924HCID 90402924, VerbindungAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

To a solution of 1-(4-methoxybenzyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propyl)-1H-purine-2,6(3H,7H)-dione (130 mg, 0.261 mmol, intermediate 60) in DMF (3 mL) was added 1-(bromomethyl)-4-chlorobenzene (70 mg, 0.345 mmol), followed by potassium carbonate (107 mg, 0.775 mmol) and TBAI (5 mg, 0.014 mmol). The mixture was stirred at 60° C. overnight. The reaction was cooled and partitioned between ethyl acetate and water. The combined organic phase was washed with brine, dried over sodium sulfate, and concentrated to give the crude product 7-(4-chlorobenzyl)-1-(4-methoxybenzyl)-3-methyl-8-(3-(3-(trifluoromethoxy)phenoxy)propyl)-1H-purine-2,6(3H,7H)-dione (150 mg, 92.5% yield) as a yellow oil. LCMS retention time 2.075 min; LCMS MH+ 629.

Aufarbeitung

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. washThe combined organic phase was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-af9107b33c6d4e50ba54065589cffa6d
Quelldatensatz
uspto-grants-2016_06
Patentnummer
US09359359B2

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