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

HRID 2401214노트

반응식

HRID 2401214 반응식
[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

참가 물질

4

반응물 2

HCID 24813Phosphorus oxychlorideHCID 178494687HCID 178494687, 화합물2회

생성물 1

HCID 143061604-Methoxymethyl-5-methyl-6-chloropyrimidine수율 91%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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);

후처리

  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

출처 및 근거

ORD 기록
ord-e792e26784f444fd86ac0d894dc23d39
출처 데이터셋
uspto-grants-2014_08
특허 번호
US08796283B2

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