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

HRID 410393Notes

Reaction equation

HRID 410393 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-ead74c6d90b14775b3e659472de33c01
Source dataset
uspto-grants-2014_06
Patent number
US08759366B2

Reaction notes

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