4,6-Dichloro-2-methylpyrimidine → 4-Chloro-2-methyl-6-(methylthio)pyrimidine

HRID 1622024Notes

Reaction equation

HRID 1622024 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([CH3:9])[N:3]=1.[CH3:10][S-:11].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([S:11][CH3:10])[N:5]=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 2349974,6-Dichloro-2-methylpyrimidineHCID 4378561Sodium methanethiolate

Product 1

HCID 569244304-Chloro-2-methyl-6-(methylthio)pyrimidineYield 60.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4,6-dichloro-2-methylpyrimidine (Aldrich) (2.000 g, 12.27 mmol) in THF (25 mL) was added sodium thiomethoxide (Aldrich) (0.903 g, 12.88 mmol). The reaction mixture was stirred at rt under N2 for 3 h. The reaction mixture was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic layers were dried over MgSO4 and concentrated. The crude product was purified by column chromatography (120 g, 5% to 10% acetone in hexanes) to afford the product as white solid (1.3 g). MS (ESI pos. ion) m/z: 174.9. 1H NMR (300 MHz, CDCl3) δ ppm 2.57 (s, 3H) 2.65 (s, 3H) 7.02 (s, 1H).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  3. dry with materialThe combined organic layers were dried over MgSO4
  4. concentrationconcentrated
  5. customThe crude product was purified by column chromatography (120 g, 5% to 10% acetone in hexanes)

Sources & evidence

ORD record
ord-0acf7732ef9a4bc69f0b2d0fe60db06f
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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