Potassium Carbonate → HCID 68982163, compound

HRID 1821645Notes

Reaction equation

HRID 1821645 reaction equation
Br[C:2]1[N:7]=[C:6]2[N:8]([CH:12]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH3:13])[C:9](=[O:11])[NH:10][C:5]2=[N:4][CH:3]=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24](B(O)O)[CH:25]=[C:26]([O:30][CH3:31])[C:27]=1[O:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:14]1([CH:12]([N:8]2[C:6]3=[N:7][C:2]([C:24]4[CH:25]=[C:26]([O:30][CH3:31])[C:27]([O:28][CH3:29])=[C:22]([O:21][CH3:20])[CH:23]=4)=[CH:3][N:4]=[C:5]3[NH:10][C:9]2=[O:11])[CH3:13])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27343903,4,5-Trimethoxybenzeneboronic acidHCID 74324247HCID 74324247, compound

Product 1

HCID 68982163HCID 68982163, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 6-bromo-1-(1-phenylethyl)-1,3-dihydroimidazo[4,5-b]pyrazin-2-one (47.2 mg, 0.15 mmol), 3,4,5-trimethoxyphenyl boronic acid (31.8 mg, 0.15 mmol) and potassium carbonate (62.2 mg, 0.45 mmol) in degassed 20% aq. dioxane (5 mL) was added dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) dichloromethane adduct (12 mg, 0.015 mmol) under an argon atmosphere. The mixture was stirred at 95° C. for 20 h, then cooled to room temperature and concentrated under reduced pressure. Purification of the resultant residue by flash chromatography [hexanes/ethyl acetate (2:1)] afforded 1-(1-phenylethyl)-6-(3,4,5-trimethoxyphenyl)-1,3-dihydro-imidazo[4,5-b]pyrazin-2-one as a white solid (36.6 mg, 60%). 1H NMR (300 MHz, DMSO): δ 12.10 (s, 1H), 8.53 (s, 1H), 7.51 (d, J=5.7 Hz, 2H), 7.33 (dd, J=5.7, 6.0 Hz, 2H), 7.26-7.22 (m, 1H), 7.23 (s, 2H), 5.71 (q, J=5.1 Hz, 1H), 3.84 (s, 6H), 3.67 (s, 3H), 1.97 (d, J=5.1 Hz, 3H). MS: 407.4 (M+H).

Workup

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

Sources & evidence

ORD record
ord-a2c72c13209c49fb81d03749f97477e5
Source dataset
uspto-grants-2009_10
Patent number
US07608622B2

Reaction notes

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