Sodium methanethiolate → 2-Chloro-4-(methylthio)pyrimidine

HRID 539900

Reaction equation

HRID 539900 reaction equation
C([C:3]1[C:4](Cl)=[N:5][C:6]([Cl:9])=[N:7][CH:8]=1)C.[CH3:11][S-:12].[Na+]>O1CCCC1.C(OCC)(=O)C>[Cl:9][C:6]1[N:5]=[C:4]([S:12][CH3:11])[CH:3]=[CH:8][N:7]=1

Participants

5

Reactant 2

HCID 4378561Sodium methanethiolateHCID 100124582,4-Dichloro-5-ethylpyrimidine

Product 1

HCID 164271482-Chloro-4-(methylthio)pyrimidineYield 53.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of ethyl 2,4-dichloropyrimidine (20.0 g, 0.13 mol) in 150 mL of anhydrous tetrahydrofurane was added sodium thiomethoxide (49.30 mL, 0.15 mol) at −10° C. The reaction mixture was allowed to warm up to room temperature and then stirred for 5 hours with monitoring a reaction with LC-MS or thin layer chromatography (TLC). The reaction mixture was diluted with ethyl acetate and washed with brine (×2). The collected organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The resulting solid was slurrified with diethyl ether and then collected by filtration to afford the desired intermediate 10 as a white solid (11.2 g, 52%)

Workup

  1. customa reaction with LC-MS or thin layer chromatography (TLC)
  2. washwashed with brine (×2)
  3. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated in vacuo
  5. filtrationcollected by filtration

Sources & evidence

ORD record
ord-4f1103dca1964454aec85ad23af160f0
Source dataset
uspto-grants-2014_10
Patent number
US08871778B2

Linked notes

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