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

HRID 896237Notes

Reaction equation

HRID 896237 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.[CH3:11][Mg+].[Br-]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH3:11])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1

Participants

4

Reactant 2

HCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 178418689HCID 178418689, compound

Product 1

HCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineYield 74.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

According to Scheme 12, a solution of 4,6-dichloro-2-methylthiopyrimidine (1.95 g, 10 mmol) in 30 mL of dry THF was cooled to 0° C. and treated with a solution of MeMgBr (14 mL of 1.4 M solution, 19.6 mmol). After overnight stirring at RT, the reaction mixture was quenched with sat. NH4Cl. The organic layer washed with brine, dried and evaporated. The residue was purified by chromatography (silica gel, hexane:ethyl acetate, 9:1) to provide 1.3 g of 4-chloro-6-methyl-2-methylthiopyrimidine (95).

Workup

  1. customthe reaction mixture was quenched with sat. NH4Cl
  2. washThe organic layer washed with brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by chromatography (silica gel, hexane:ethyl acetate, 9:1)

Sources & evidence

ORD record
ord-aa26f250983441a38aa20a57ec12143b
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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