Sodium Carbonate → HCID 59242786, compound

HRID 1514407Notes

Reaction equation

HRID 1514407 reaction equation
Cl[C:2]1[C:7]([CH3:8])=[CH:6][N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13](B(O)O)[CH:12]=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]>[CH3:8][C:7]1[C:2]([C:13]2[CH:12]=[N:11][CH:16]=[CH:15][CH:14]=2)=[N:3][C:4]([S:9][CH3:10])=[N:5][CH:6]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343783-Pyridinylboronic acidHCID 235627084-Chloro-5-methyl-2-(methylthio)pyrimidine

Product 1

HCID 59242786HCID 59242786, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

A mixture of 4-chloro-5-methyl-2-methylsulfanyl-pyrimidine (1.24 g, 7.1 mmol), pyridine-3-boroni acid (1.04 g, 8.46 mmol), Na2CO3 (863 mg, 7.76 mmol), PPh3 (186 mg, 0.71 mmol) and Pd(OAc)2 (40 mg) in n-PrOH (50 ml) was refluxed for 2 hours. The solvent was then evaporated under vacuum and the crude was partitioned between water and ethyl acetate. The organic phase was dried (Na2SO4) and evaporated. The crude was purified by flash chromatography with ethyl acetate-petroleum ether (1-1) to afford 1.28 g of the title compound as a white solid (83% yield)

Workup

  1. temperaturewas refluxed for 2 hours
  2. customThe solvent was then 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 purified by flash chromatography with ethyl acetate-petroleum ether (1-1)

Sources & evidence

ORD record
ord-0a5c9c88d09640389617b25114ba2b8b
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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