Dimethylformamide → (S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-one

HRID 388095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 388095
Br[C:2]1[N:3]=[C:4]2[N:10]([C@H:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH3:12])[C:9](=[O:19])[N:8]([CH3:20])[C:5]2=[N:6][CH:7]=1.BrC1N=C2N([C@H:32]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[CH3:33])C(=O)NC2=NC=1.C(=O)([O-])[O-].[Cs+].[Cs+].COS(OC)(=O)=O.[CH3:53][N:54](C)C=O>>[CH3:20][N:8]1[C:5]2=[N:6][CH:7]=[C:2]([C:39]3[CH:38]=[CH:37][CH:36]=[C:35]4[C:34]=3[CH:32]=[CH:33][CH:53]=[N:54]4)[N:3]=[C:4]2[N:10]([C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH3:12])[C:9]1=[O:19]

Komponenten

6

Edukt 5

HCID 6228DimethylformamideHCID 6497Dimethyl SulfateHCID 10796Cesium carbonateHCID 24815573(S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2-olHCID 86626387(S)-5-Bromo-1-methyl-3-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one

Produkt 1

HCID 66699676(S)-1-Methyl-3-(1-phenylethyl)-5-(quinolin-5-YL)-1H-imidazo[4,5-B]pyrazin-2(3H)-oneAusbeute 83 %

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

(S)-5-Bromo-1-methyl-3-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one. To a solution of (S)-6-bromo-1-(1-phenylethyl)-1H-imidazo[4,5-b]pyrazin-2(3H)-one (0.300 g, 0.943 mmol) in dimethylformamide (3 mL) was added cesium carbonate (excess) followed by dimethylsulfate (0.130 g, 1.03 mmol). The solution was heated to 55° C. in a screw capped tube. After one hour, the solution was filtered to remove cesium carbonate salts. The filtrate was condensed under reduced pressure and the crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes) to afford the title compound (0.306 g, 83% yield). 1H NMR (300 MHz, DMSO-d6) δ 7.99 (s, 1H), 7.57 (d, 2H), 7.32 (m, 3H), 5.77 (q, 1H), 3.42 (s, 3H), 2.04 (d, 3H); 13C NMR (75 MHz, CHCl3) δ 52.6 (C═O); MS (ESI) m/z 333.3 [M+1]+, 335.3 [M+2]+.

Aufarbeitung

  1. customcapped tube
  2. filtrationthe solution was filtered
  3. customto remove cesium carbonate salts
  4. customcondensed under reduced pressure
  5. customthe crude product purified via Biotage silica gel chromatography (5-50% ethyl acetate/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-1890afea18c54a2f835af4390df6a463
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372976B2

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