4,6-Dichloropyrimidine → 4-Chloro-6-(methylsulfanyl)pyrimidine

HRID 659025Notes

Reaction equation

HRID 659025 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[CH:4][N:3]=1.[CH3:9][S-:10].[Na+]>C1COCC1.C(OCC)(=O)C.O>[Cl:1][C:2]1[CH:7]=[C:6]([S:10][CH3:9])[N:5]=[CH:4][N:3]=1

Participants

6

Reactant 2

HCID 709434,6-DichloropyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 218130774-Chloro-6-(methylsulfanyl)pyrimidineYield 90.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 4,6-dichloro-pyrimidine (10.0 g, 67 mmol) in THF (55 ml), sodium thiomethylate (5.175 g, 74 mmol) is added under inert gas atmosphere. The reaction mixture is stirred at 60° C. overnight. After cooling down to r.t., the reaction mixture is diluted with ethyl acetate and water (100 ml each). The organic phase is removed and the aqueous phase is extracted with ethyl actetate. The combined organic phases are washed and dried, and the solvent is evaporated to give 9.74 g (90%) of a pale yellow solid (contains ca. 9% of starting material and ca. 9% of 4,6-dimethylsulfanyl-pyrimidine) which is used without any further purification.

Workup

  1. temperatureAfter cooling down to r.t.
  2. customThe organic phase is removed
  3. extractionthe aqueous phase is extracted with ethyl actetate
  4. washThe combined organic phases are washed
  5. customdried
  6. customthe solvent is evaporated

Sources & evidence

ORD record
ord-e94874e78eb84824a8768f65a083e4fc
Source dataset
uspto-grants-2011_12
Patent number
US08080552B2

Reaction notes

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