Hydrazine hydrate (1:1) → 5-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide

HRID 507640ノート

反応式

HRID 507640 の反応式
[Cl:1][C:2]1[C:3]([C:10]([OH:12])=O)=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1.O.[NH2:14][NH2:15]>C1COCC1.O>[Cl:1][C:2]1[C:3]([C:10]([NH:14][NH2:15])=[O:12])=[N:4][C:5]([S:8][CH3:9])=[N:6][CH:7]=1

参加物

5

反応物 2

HCID 24654Hydrazine hydrate (1:1)HCID 7257115-Chloro-2-(methylsulfanyl)pyrimidine-4-carboxylic acid

生成物 1

HCID 432447685-Chloro-2-(methylthio)pyrimidine-4-carbohydrazide収率 58%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

5-Chloro-2-(methylthio)pyrimidine-4-carboxylic acid (4.0 g, 19.6 mmol) and 1,1-carbonyl diimidazole (6.35 g, 39.2 mmol) were dissolved in 80 mL THF and stirred at room temperature. After 3 h, the solution was cooled with an ice bath and hydrazine hydrate (1.90 mL, 39.2 mmol) was added in one quick portion. The solution was allowed to stir for 5 h, gradually warming to room temperature. The reaction mixture was diluted with excess H2O and extracted with EtOAc several times. These organics were combined and washed with 2 N HCl. The combined aqueous layers were then basified carefully with 5 N NaOH, and extracted once again with EtOAc. This second set of organic layers were combined, dried over magnesium sulfate and concentrated under vacuum to give 2.46 g (58% yield) of product as a white solid. MS (M+H)+ 219.

後処理

  1. temperaturethe solution was cooled with an ice bath
  2. stirringto stir for 5 h
  3. temperaturegradually warming to room temperature
  4. extractionextracted with EtOAc several times
  5. washwashed with 2 N HCl
  6. extractionextracted once again with EtOAc
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated under vacuum

出典と根拠

ORDレコード
ord-175d6a427f68456b92fd83c52da47dbe
出典データセット
uspto-grants-2010_08
特許番号
US07786132B2

反応ノート

読み込み中…