2,4-Dichloropyrimidine → 2-Chloro-4-(methylthio)pyrimidine

HRID 1039883Notes

Reaction equation

HRID 1039883 reaction equation
[CH3:1][S-:2].[Na+].[Cl:4][C:5]1[N:10]=[C:9](Cl)[CH:8]=[CH:7][N:6]=1>C1COCC1.C(OCC)(=O)C>[Cl:4][C:5]1[N:10]=[C:9]([S:2][CH3:1])[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 2

HCID 775312,4-DichloropyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 164271482-Chloro-4-(methylthio)pyrimidineYield 70.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium thiomethoxide (5.18 g, 73.8 mmol) was added slowly portion-wise via powder addition funnel to a stirring solution of 2,4-dichloropyrimidine (10 g, 67.1 mmol) in THF (150 mL) at room temperature. After stirring overnight, the reaction was taken up in ethyl acetate, washed with water, brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with ethyl acetate and hexanes to give 2-chloro-4-(methylsulfanyl)pyrimidine (10.127 g, 47.3 mmol, 70.4%) as a white solid.

Workup

  1. washwashed with water, brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel eluting with ethyl acetate and hexanes

Sources & evidence

ORD record
ord-e769dedf1548485b872c635ee890d3e9
Source dataset
uspto-grants-2013_10
Patent number
US08551984B2

Reaction notes

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