Methanol → HCID 68283586、化合物

HRID 624083ノート

反応式

HRID 624083 の反応式
Cl[C:2]1[C:7]([CH3:8])=[C:6](Cl)[N:5]=[C:4]([S:10][CH3:11])[N:3]=1.[CH3:12][O-:13].[Na+].[CH3:15][OH:16]>>[CH3:12][O:13][C:2]1[C:7]([CH3:8])=[C:6]([O:16][CH3:15])[N:5]=[C:4]([S:10][CH3:11])[N:3]=1

参加物

4

反応物 3

HCID 887MethanolHCID 10942334Sodium Methoxide2 回HCID 220024654,6-Dichloro-5-methyl-2-(methylthio)pyrimidine

生成物 1

HCID 68283586HCID 68283586、化合物

実験手順

To an ice-cooled solution of 4,6-dichloro-5-methyl-2-(methylthio)pyrimidine (607 mg, 2.903 mmol) in MeOH (7 mL), NaOMe (1.25 g, 23.23 mmol) was added portionwise. The brown suspension was slowly allowed to reach rt, stirred at rt for 18 h and refluxed (85° C.) for 3 h. Due to the fact that the reaction was not completed, 0.4 eq. of NaOMe was added and the dark yellow suspension was refluxed (85° C.) for another 18 h. The reaction mixture was allowed to reach rt, then the solvent was removed and the residue was redissolved in EtOAc. The org. layer was washed with water, the aq. layer was reextracted with EtOAc (100 mL) and the combined org. layers were washed with brine, dried (MgSO4), filtered and the solvent was removed under reduced pressure. Purification by FC (EtOAc/hept 3:97) yielded 4,6-dimethoxy-5-methyl-2-(methylthio)pyrimidine as a solid. LC-MS conditions A: tR=0.93 min, [M+H]+=201.12.

後処理

  1. additionwas added portionwise
  2. customto reach rt
  3. temperaturerefluxed (85° C.) for 3 h
  4. temperaturethe dark yellow suspension was refluxed (85° C.) for another 18 h
  5. customto reach rt
  6. customthe solvent was removed
  7. dissolutionthe residue was redissolved in EtOAc
  8. washlayer was washed with water
  9. washlayers were washed with brine
  10. dry with materialdried (MgSO4)
  11. filtrationfiltered
  12. customthe solvent was removed under reduced pressure
  13. customPurification by FC (EtOAc/hept 3:97)

出典と根拠

ORDレコード
ord-e21d980de4aa44ffb638f4ddbffb1776
出典データセット
uspto-grants-2016_04
特許番号
US09303023B2

反応ノート

読み込み中…