Sodium Carbonate → HCID 58994150, compound

HRID 12733

Reaction equation

HRID 12733 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.[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1Br.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]>[CH3:14][C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[C:6]1[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 8176303-Bromo-4-methylpyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Product 1

HCID 58994150HCID 58994150, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxypyrimidine-5-boronic acid (1.3 g, 7.23 mmol) was dissolved in degassed n-PrOH (20 ml) and then 4-methyl-3-bromo-pyridine (830 g, 4.82 mmol), Na2CO3 (1.02 g, 9.64 mmol), PPh3 (126 mg, 0.48 mmol) and Pd(OAc)2 (40 mg) were added. The suspension was stirred at reflux for 3 hours. The solvent was evaporated under vacuum and the crude was partitioned between water and DCM. The organic phase was dried (Na2SO4) and evaporated to give the title compound that was used without further purification in the next step (quantitative yield).

Workup

  1. temperatureat reflux for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. customthe crude was partitioned between water and DCM
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. customevaporated

Sources & evidence

ORD record
ord-a66b7a3b045043e6b8987f76f458da43
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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