Sodium Carbonate → HCID 58994172, compound

HRID 12740Notes

Reaction equation

HRID 12740 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[N:16]=[N:17][CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[Na+].[Na+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3]1[N:8]=[C:7]([O:9][CH3:10])[C:6]([C:15]2[N:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[CH:5][N:4]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acidHCID 112986823-Iodopyridazine

Product 1

HCID 58994172HCID 58994172, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-pyrimidine-5-boronic acid (2.05 g, 11.21 mmol) was dissolved in degassed n-PrOH (80 ml) and then 3-iodo-pyridazine (Prep 119, 2.1 g, 10.19 mmol), Na2CO3 (3.24 g, 30.57 mmol), PPh3 (890 mg, 3.40 mmol) and Pd(OAc)2 (180 mg, 0.8 mmol) were added. The suspension was stirred at reflux for 5 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase washed with brine, dried (Na2SO4) and evaporated. The residue was triturated with iPrOH to afford 750 mg of the title compound as a white powder (34% yield).

Workup

  1. temperatureat reflux for 5 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and ethyl acetate
  4. washThe organic phase washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was triturated with iPrOH

Sources & evidence

ORD record
ord-61ffd24111f1436bb4e1532169ca5db5
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Reaction notes

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