Phosphorus oxychloride → 4-Methoxymethyl-5-methyl-6-chloropyrimidine

HRID 2401214ノート

反応式

HRID 2401214 の反応式
[CH3:1][C:2]1[C:3](O)=[N:4][CH:5]=[N:6][C:7]=1[CH2:8][O:9][CH3:10].P(Cl)(Cl)([Cl:14])=O>C(Cl)Cl>[Cl:14][C:3]1[C:2]([CH3:1])=[C:7]([CH2:8][O:9][CH3:10])[N:6]=[CH:5][N:4]=1

参加物

4

反応物 2

HCID 24813Phosphorus oxychlorideHCID 178494687HCID 178494687、化合物2 回

生成物 1

HCID 143061604-Methoxymethyl-5-methyl-6-chloropyrimidine収率 91%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

5-Methyl-6-[(methyloxy)methyl]-4-pyrimidinol (Intermediate 48, 2.10 g, 13.62 mmol) was dissolved in DCM (20 ml), treated with phosphorus oxychloride (12.04 ml, 129 mmol) and the resulting mixture was heated under reflux for 3 hours, allowed to cool to room temperature and left to stand overnight. The solvent was removed under reduced pressure, the residue taken up in ice water and the pH was adjusted to 7 using aqueous 2M sodium hydroxide solution. The mixture was extracted with chloroform (×3) and the chloroform layers were separated, combined, dried under magnesium sulfate and evaporated under reduced pressure. The residue was purified by SP4 Biotage column chromatography eluting with a gradient of 0-50% ethyl acetate and iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound as a yellow oil (2.14 g);

後処理

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 3 hours
  3. waitleft
  4. customThe solvent was removed under reduced pressure
  5. extractionThe mixture was extracted with chloroform (×3)
  6. customthe chloroform layers were separated
  7. customdried under magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was purified by SP4 Biotage column chromatography
  10. washeluting with a gradient of 0-50% ethyl acetate and iso-hexane
  11. additionProduct containing fractions
  12. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-e792e26784f444fd86ac0d894dc23d39
出典データセット
uspto-grants-2014_08
特許番号
US08796283B2

反応ノート

読み込み中…