Phosphorus oxychloride → 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

HRID 1795450노트

반응식

HRID 1795450 반응식
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11](O)=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1.O=P(Cl)(Cl)[Cl:25].C([O-])(O)=O.[Na+]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9](=[O:22])[N:10]([CH3:21])[C:11]([Cl:25])=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 1784816025-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

생성물 1

HCID 221851865-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
85 °C

실험 절차

To a 250 mL RBF, was added 5-(3-bromo-phenyl)-2-hydroxy-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one (5.76 g, 16.1 mmol), 50 mL POCl3. The mixture was warmed up to 85° C. and stirred for 15 h under nitrogen. The mixture was cooled down to rt and vacuumed down all volatile composites. The black cake obtained was dissolved in dichloromethane, neutralized with sat. NaHCO3. After purified by flash chromatography, the 5-(3-Bromo-phenyl)-2-chloro-3-methyl-6-pyridin-4-yl-3H-pyrimidin-4-one was obtained in 4.72 g as white powder. MS (ES+): 376 (M+H)+; (ES−): 374 (M−H).

후처리

  1. temperatureThe mixture was cooled down to rt
  2. customThe black cake obtained
  3. customAfter purified by flash chromatography

출처 및 근거

ORD 기록
ord-271920d04eb14f02b0b5df2e8d91ff26
출처 데이터셋
uspto-grants-2006_04
특허 번호
US07026326B2

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