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

HRID 216267ノート

反応式

HRID 216267 の反応式
[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

参加物

5

反応物 4

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

生成物 1

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

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-5dfaa9a6349348c8824b723b0deed199
出典データセット
uspto-grants-2012_06
特許番号
US08193183B2

反応ノート

読み込み中…