Potassium Carbonate → 8-{1-[3-(4-Fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

HRID 925554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925554
[CH2:1]([N:4]1[C:12](=[O:13])[C:11]2[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:9]([C:22]3[CH:23]=[N:24][NH:25][CH:26]=3)=[N:8][C:7]=2[N:6]=[C:5]1[N:27]1[CH2:31][CH2:30][CH2:29][CH2:28]1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Br[CH2:39][C:40]#[C:41][C:42]1[CH:47]=[CH:46][C:45]([F:48])=[CH:44][CH:43]=1>CC(C)=O>[F:48][C:45]1[CH:46]=[CH:47][C:42]([C:41]#[C:40][CH2:39][N:24]2[CH:23]=[C:22]([C:9]3[N:10]([CH2:14][O:15][CH2:16][CH2:17][Si:18]([CH3:21])([CH3:20])[CH3:19])[C:11]4[C:12](=[O:13])[N:4]([CH2:1][CH2:2][CH3:3])[C:5]([N:27]5[CH2:28][CH2:29][CH2:30][CH2:31]5)=[N:6][C:7]=4[N:8]=3)[CH:26]=[N:25]2)=[CH:43][CH:44]=1

Komponenten

5

Edukt 3

HCID 11430Potassium CarbonateHCID 105605241-(3-Bromoprop-1-yn-1-yl)-4-fluorobenzeneHCID 671351511-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one

Produkt 1

HCID 671350228-{1-[3-(4-Fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-oneAusbeute 22 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 1-Propyl-8-(1H-pyrazol-4-yl)-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.111 g, 0.25 mmol), potassium carbonate (0.052 g, 0.38 mmol), 1-(3-bromo-prop-1-ynyl)-4-fluoro-benzene (0.69 g, 0.33 mmol) was taken in acetone (10 ml). The reaction mixture was heated at 80° C. for 2 hours. The mixture was cooled to room temperature and filtered through sintered funnel, washed with acetone. Solvent was evaporated and the residue was purified by preparative TLC to obtain pure 8-{1-[3-(4-Fluoro-phenyl)-prop-2-ynyl]-1H-pyrazol-4-yl}-1-propyl-2-pyrrolidin-1-yl-7-(2-trimethylsilanyl-ethoxymethyl)-1,7-dihydro-purin-6-one (0.025 g, 22%) as colourless oil.

Aufarbeitung

  1. temperatureThe mixture was cooled to room temperature
  2. filtrationfiltered through sintered funnel
  3. washwashed with acetone
  4. customSolvent was evaporated
  5. customthe residue was purified by preparative TLC

Quellen und Nachweise

ORD-Eintrag
ord-b02fc6a8dbe146c186a15caf6f987a92
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284316B2

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