4,6-Dichloro-2-(methylthio)pyrimidine → 4-Chloro-6-methyl-2-(methylthio)pyrimidine
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]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
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
- customthe reaction mixture was quenched with sat. NH4Cl
- washThe organic layer washed with brine
- customdried
- customevaporated
- 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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