Potassium Carbonate → 1-(3-Nitrobenzyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one

HRID 1821651Notes

Reaction equation

HRID 1821651 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([N+:19]([O-:21])=[O:20])[CH:14]=3)[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.[CH3:22][O:23][C:24]1[CH:25]=[C:26](B(O)O)[CH:27]=[C:28]([O:32][CH3:33])[C:29]=1[O:30][CH3:31].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C1C=CC([PH+]([C]2[CH][CH][CH][CH]2)C2C=CC=CC=2)=CC=1.C(Cl)Cl.Cl[Pd]Cl.[Fe]>[N+:19]([C:15]1[CH:14]=[C:13]([CH:18]=[CH:17][CH:16]=1)[CH2:12][N:8]1[C:6]2=[N:7][C:2]([C:26]3[CH:27]=[C:28]([O:32][CH3:33])[C:29]([O:30][CH3:31])=[C:24]([O:23][CH3:22])[CH:25]=3)=[CH:3][N:4]=[C:5]2[NH:10][C:9]1=[O:11])([O-:21])=[O:20]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 57893433HCID 57893433, compound

Product 1

HCID 115249241-(3-Nitrobenzyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-oneYield 70%

Reagents, catalysts & solvents 2

HCID 53485975CID 53485975CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-bromo-1-(3-nitrobenzyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one (95 mg, 0.27 mmol), 3,4,5-trimethoxyphenyl boronic acid (65 mg, 0.30 mmol) and potassium carbonate (120 mg, 0.88 mmol) in degassed 20% aq. dioxane (2.5 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (24 mg, 0.029 mmol) under an argon atmosphere. The mixture was stirred at 95° C. overnight, then cooled to room temperature and concentrated under reduced pressure. Purification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)] afforded 1-(3-nitrobenzyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one as a white solid (82 mg, 70%). 1H NMR (300 MHz, CDCl3): δ 8.48 (t, J=2.2 Hz, 1H), 8.19 (dd, J=7.5 and 2.2 Hz, 1H), 7.91 (dd, J=7.5 and 2.2 Hz, 1H), 7.55 (t, J=7.5 Hz, 1H), 7.16 (s, 2H), 5.30 (s, 2H), 4.00 (s, 6H), 3.92 (s, 3H). MS: 438.1 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. customPurification of the resultant residue by flash chromatography [silica gel; hexanes/ethyl acetate (2:1)]

Sources & evidence

ORD record
ord-716cd2a35c90453e8f8460f2b0ca25bf
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

Loading…