Sodium Carbonate → 5-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidine

HRID 12703

Reaction equation

HRID 12703 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.Br[C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[N:16]=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]>[F:21][C:17]1[N:16]=[C:15]([C:6]2[C:7]([O:9][CH3:10])=[N:8][C:3]([O:2][CH3:1])=[N:4][CH:5]=2)[CH:20]=[CH:19][CH:18]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 6394382-Bromo-6-fluoropyridineHCID 2736209(2,4-Dimethoxypyrimidin-5-yl)boronic acid

Product 1

HCID 589942165-(6-Fluoro-pyridin-2-yl)-2,4-dimethoxy-pyrimidineYield 57.6%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

2,4-Dimethoxy-pyrimidine-5-boronic acid (966 mg, 5.3 mmol) was dissolved in degassed n-PrOH (60 ml) and then 2-bromo-6-fluoropyridine (850 mg, 4.8 mmol), Na2CO3 (1.676 g, 15.8 mmol), PPh3 (400 mg, 1.52 mmol) and Pd(OAc)2 (116 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 ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was triturated with iPrOH to give 650 mg of the title compound as a white powder (52% yield).

Workup

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

Sources & evidence

ORD record
ord-f8171c7006b0492aa5e0fccdfb9481a4
Source dataset
uspto-grants-2010_06
Patent number
US07727988B2

Linked notes

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