Hydrochloric Acid → 1-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid

HRID 2110795노트

반응식

HRID 2110795 반응식
[CH3:1][O:2][CH:3]1[N:8](Cl)[CH:7]=[CH:6][C:5]([Cl:10])=[N:4]1.Cl.[C:12](=[O:15])(O)[O-:13].[Na+].[CH3:17][CH2:18]O>>[Cl:10][C:5]1[N:4]=[C:3]([O:2][CH3:1])[N:8]=[C:7]([N:4]2[CH2:18][CH2:17][CH:7]([C:12]([OH:13])=[O:15])[CH2:6][CH2:5]2)[CH:6]=1

참가 물질

5

반응물 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 516892Sodium BicarbonateHCID 866157142-Methoxy-3,6-dichloropyrimidine

생성물 1

HCID 862401201-(6-Chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid수율 70%

반응 조건

온도
90 °C

실험 절차

A mixture of 2-methoxy-3,6-dichloropyrimidine (635 mg, 3.55 mmol), isonipecotic hydrochloride (706 mg, 4.26 mmol) and sodium bicarbonate (895 mg, 10.65 mmol) in EtOH (12 mL) is heated at 90° C. for 15 hours. The mixture is concentrated, and the residue is taken up in water (30 mL) and extracted three times with EtOAc (25 mL). The aqueous solution is acidified to pH 3 with 10% citric acid and extracted three times with EtOAc (25 mL). The organic extracts from the acidic layer are combined and dried over magnesium sulfate, filtered and concentrated to afford 1-(6-chloro-2-methoxy-pyrimidin-4-yl)-piperidine-4-carboxylic acid [680 mg, 70%] as a solid.

후처리

  1. concentrationThe mixture is concentrated
  2. extractionextracted three times with EtOAc (25 mL)
  3. extractionextracted three times with EtOAc (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-6c4a7955f7d94c76a6c734e74048b403
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07517889B2

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