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

HRID 1014690Notes

Reaction equation

HRID 1014690 reaction equation
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]

Participants

6

Reactant 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

Product 1

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

Conditions

Temperature
55 °C

Procedure

(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]+.

Workup

  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)

Sources & evidence

ORD record
ord-5e4b5d3d6f8a4cc5abe40b43193d8a44
Source dataset
uspto-grants-2011_07
Patent number
US07981893B2

Reaction notes

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