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

HRID 629022ノート

反応式

HRID 629022 の反応式
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

参加物

4

反応物 3

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

生成物 1

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

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-fe51c7f26c1846cd9f789ed38991ea52
出典データセット
uspto-grants-2016_04
特許番号
US09315491B2

反応ノート

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