2,4-Dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine → 2-Chlorobenzo[4,5]thieno[2,3-d]pyrimidine

HRID 711396Notes

Reaction equation

HRID 711396 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[S:15]C(Cl)(Cl)Cl)=[CH:4][N:3]=1>CN(C=O)C.O.[Cu]I>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[S:15][C:4]=2[N:3]=1

Participants

5

Reactant 1

HCID 1183402992,4-Dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine

Product 1

HCID 918846182-Chlorobenzo[4,5]thieno[2,3-d]pyrimidineYield 38.4%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
110 °C

Procedure

A solution of 2,4-dichloro-5-(2-((trichloromethyl)thio)phenyl)pyrimidine (0.618 g, 1.650 mmol) and copper(I) iodide (0.031 g, 0.165 mmol) in DMF (24.63 ml) was degassed with nitrogen and heated at 110° C. overnight. The reaction solution was cooled to room temperature, diluted with water and filtered. The resulting brown solids were washed with water and a small volume of EtOH. The aqueous layer was extracted twice with EtOAc, combined with the solids, and concentrated in vacuo. The crude product was purified by column chromatography on silica gel, eluted with 10-20% EtOAc/heptanes (v/v), affording 0.14 g (38% yield) of the 2-chlorobenzo[4,5]thieno[2,3-d]pyrimidine as white solids.

Workup

  1. temperatureThe reaction solution was cooled to room temperature
  2. filtrationfiltered
  3. washThe resulting brown solids were washed with water
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography on silica gel
  7. washeluted with 10-20% EtOAc/heptanes (v/v)

Sources & evidence

ORD record
ord-fca663239ad443d5b3f0140c3f657992
Source dataset
uspto-grants-2015_11
Patent number
US09181270B2

Reaction notes

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