HCID 12793231, compound → [2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-chloro-5-methylsulfanyl-phenyl)-methanone

HRID 229406Notes

Reaction equation

HRID 229406 reaction equation
Br[C:2]1[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])=[N:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][C:10]=2[F:16])=[N:6][CH:7]=1.C([Mg]Cl)(C)C.[Cl:31][C:32]1[CH:40]=[CH:39][C:38]([S:41][CH3:42])=[CH:37][C:33]=1[C:34](Cl)=[O:35]>C1COCC1>[F:16][C:10]1[CH:11]=[C:12]([F:15])[CH:13]=[CH:14][C:9]=1[O:8][C:5]1[N:4]=[C:3]([O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][C:19]=2[F:25])[C:2]([C:34]([C:33]2[CH:37]=[C:38]([S:41][CH3:42])[CH:39]=[CH:40][C:32]=2[Cl:31])=[O:35])=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 12793231HCID 12793231, compoundHCID 59834408HCID 59834408, compoundHCID 178418918HCID 178418918, compound

Product 1

HCID 57758593[2,4-Bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-chloro-5-methylsulfanyl-phenyl)-methanoneYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To 5-bromo-2,4-bis-(2,4-difluoro-phenoxy)-pyrimidine (3.83 g, 9.23 mmol) in dry THF at 0° C. was added isopropyl magnesium chloride (6.93 mL of 2.0 M solution in THF, 13.85 mmol). The resulting mixture was stirred at 0° C. for 20 minutes. A solution of 2-chloro-5-methylsulfanyl-benzoyl chloride (4.27 g, 19.33 mmol) in 20 mL dry THF was added dropwise, with stirring at 0° C. continued for one hour. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was separated, washed with saturated brine, dried over MgSO4, filtered and concentrated under reduced pressure. The residue was chromatographed through silica gel (EtOAc/hexanes 5-25%) to give 3.015 g of [2,4-bis-(2,4-difluoro-phenoxy)-pyrimidin-5-yl]-(2-chloro-5-methylsulfanyl-phenyl)-methanone, MS (M+H)=521.

Workup

  1. stirringwith stirring at 0° C.
  2. waitcontinued for one hour
  3. customThe reaction mixture was partitioned between water and ethyl acetate
  4. customthe organic layer was separated
  5. washwashed with saturated brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was chromatographed through silica gel (EtOAc/hexanes 5-25%)

Sources & evidence

ORD record
ord-05959e29543f436e92b16d3850075ab4
Source dataset
uspto-grants-2009_07
Patent number
US07563799B2

Reaction notes

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