Potassium Carbonate → HCID 86725461, compound

HRID 1754586Notes

Reaction equation

HRID 1754586 reaction equation
Br[C:2]1[N:10]([CH3:11])[C:9]2[C:8](=[O:12])[N:7]([CH3:13])[C:6](=[O:14])[N:5]([CH3:15])[C:4]=2[N:3]=1.[CH3:16][O:17][C:18]1[CH:19]=[C:20](B(O)O)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25].C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:13][N:7]1[C:8](=[O:12])[C:9]2[N:10]([CH3:11])[C:2]([C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[C:23]([O:24][CH3:25])[CH:22]=3)=[N:3][C:4]=2[N:5]([CH3:15])[C:6]1=[O:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 64127XanthobineHCID 27347023,4-Dimethoxyphenylboronic acid

Product 1

HCID 86725461HCID 86725461, compound

Reagents, catalysts & solvents 2

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
70 °C

Procedure

A solution of 8-Bromo-1,3,7-trimethyl xanthine (315 mg, 1.15 mmol) and 3,4-dimethoxy phenylboronic acid (230 mg; 1.26 mmol) in 1,4-dioxane (5 ml) was treated tetrakis(triphenyl phosphine) palladium (0) (88 mg, 0.14 mmol) and potassium carbonate (277 mg, 2.0 mmol). The mixture was heated to 70° C. for 12 hrs under argon atmosphere. The reaction mixture was concentrated under reduced pressure. The residue was purified on a silica gel column eluting with 70% ethyl acetate in hexane to 100% ethyl acetate. The desired product was isolated as off white solid, Yield 297 mg, 78% PRO-04-46

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was purified on a silica gel column
  3. washeluting with 70% ethyl acetate in hexane to 100% ethyl acetate

Sources & evidence

ORD record
ord-eeb171e4b191430f9cf3bb3be7ec1333
Source dataset
uspto-grants-2015_10
Patent number
US09169255B2

Reaction notes

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