Sodium Carbonate → 4-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidine

HRID 1514431Notes

Reaction equation

HRID 1514431 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C(O)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[F:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1

Participants

7

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 971134-Chloro-2-methylthiopyrimidineHCID 27343542-Fluorophenylboronic acid

Product 1

HCID 592427874-(2-Fluoro-phenyl)-2-methylsulfanyl-pyrimidineYield 90%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 10311-PropanolSolvent

Procedure

To a solution of 4-chloro-2-methylsulfanyl-pyrimidine (1.00 g, 6.22 mmol), 2-fluoro-phenyl-boronic acid (1.04 g, 6.84 mmol), Na2CO3 (790 mg, 7.45 mmol), triphenylphosphine (163 mg, 0.62 mmol) in nPrOH (50 ml), Pd(OAc)2 (42 mg, 0.187 mmol) was added and the mixture was refluxed for 3 hours. The solvent was evaporated under vacuum, and the crude was dissolved in ethyl acetate and washed with water. The organic phase was dried (Na2SO4) and evaporated; the crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5) to give the title compound (1.23 g, 90% yield).

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. customThe solvent was evaporated under vacuum
  3. dissolutionthe crude was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. customevaporated
  7. customthe crude was purified by flash chromatography with petroleum ether-ethyl acetate (97-3 to 95-5)

Sources & evidence

ORD record
ord-d75b0e9e055c4634b925646c60f3d7e8
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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