Methanol → 4-Chloro-2,6-dimethoxy-5-(methylsulfanyl)pyrimidine

HRID 629022Notes

Reaction equation

HRID 629022 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[C:5]([S:9][CH3:10])=[C:4]([Cl:11])[N:3]=1.[CH3:12][O-:13].[Na+].[CH3:15][OH:16]>>[Cl:11][C:4]1[C:5]([S:9][CH3:10])=[C:6]([O:13][CH3:12])[N:7]=[C:2]([O:16][CH3:15])[N:3]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 10942334Sodium MethoxideHCID 122255442,4,6-Trichloro-5-methylsulfanyl-pyrimidine

Product 1

HCID 155903704-Chloro-2,6-dimethoxy-5-(methylsulfanyl)pyrimidineYield 70.2%

Procedure

A mixture of 2,4,6-trichloro-5-methylsulfanyl-pyrimidine (5.00 g, 21.73 mmol.) was added dropwise to a slurry of sodium methoxide (2.47 g, 45.65 mmol, 2.1 eq) in MeOH (80 ml) in ice bath at 0° C., then the reaction mixture was stirred at r.t, for 2 hrs and dried, and the solvent was evaporated. The reaction mixture was partitioned between EA and 0.1 N HCl. The organic layer was washed with brine, dried over MgSO4, filtered and evaporated in vacuo. The resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 9:1) to give a gray solid 3.36 g (70.2%).

Workup

  1. customdried
  2. customthe solvent was evaporated
  3. customThe reaction mixture was partitioned between EA and 0.1 N HCl
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe resulting residue was purified by flash chromatography on silica gel (Hexane/EtOAc 9:1)

Sources & evidence

ORD record
ord-fe51c7f26c1846cd9f789ed38991ea52
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

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