Methanol → HCID 57498037, compound

HRID 855646Notes

Reaction equation

HRID 855646 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6](B(O)O)=[CH:5][N:4]=1.I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].CO>CS(C)=O.ClCCl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:5][N:4]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 11575IodobenzeneHCID 62657Potassium Phosphate, TribasicHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Product 1

HCID 57498037HCID 57498037, compoundYield 75%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To 2,4-Dimethoxypyrimidine-5-boronic acid (200 mg, 10.6 mmol), Iodobenzene (326 mg, 1.60 mmol) and K3PO4 (900 mg, 4.24 mmol) in DMSO (5 mL, purged with Ar) was added 1,1′bis(diphenylphosphino)ferrocene palladium chloride, complex with dichloromethane (12 mg) and the reaction solution was heated to 60 C in a sealed tube. The solution was heated for 2 h, stirred at room temperature for 10 hr and filtered through celite. The solution was poured into sat. NaHCO3 to give a gray solid. This material was collected, dissolved in ethyl acetate, dried (Na2SO4). Flash chromatography 0 to 2% methanol in dichloromethane gave 2,4-Dimethoxy-5-phenyl-pyrimidine (171 mg, 75% yield). HPLC tr=5.62 min (83%), FIA m/e 217.2 (M+H), HNMR (500 MHz, CDCl3); δ8.25 (1H, s), 7.45–7.29 (5H, m), 4.00 (3H, s), 3.98 (3H, s).

Workup

  1. temperaturethe reaction solution was heated to 60 C in a sealed tube
  2. temperatureThe solution was heated for 2 h
  3. filtrationfiltered through celite
  4. additionThe solution was poured into sat. NaHCO3
  5. customto give a gray solid
  6. customThis material was collected
  7. dissolutiondissolved in ethyl acetate
  8. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-4a75ffceeb5141fcb87214233df6acde
Source dataset
uspto-grants-2007_08
Patent number
US07262200B2

Reaction notes

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