4-Amino-6-chloropyrimidine → 4-(6-Chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester

HRID 1020025

反応式

HRID 1020025 の反応式
[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](Cl)=[O:18])[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:20][C:21]1[CH:26]=[C:25]([Cl:27])[N:24]=[CH:23][N:22]=1>CN(C1C=CN=CC=1)C.ClCCl>[CH2:1]([O:8][C:9]([N:11]1[CH2:16][CH2:15][CH:14]([C:17](=[O:18])[NH:20][C:21]2[CH:26]=[C:25]([Cl:27])[N:24]=[CH:23][N:22]=2)[CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

5

反応物 2

HCID 2380124-Amino-6-chloropyrimidineHCID 2776270Benzyl 4-(chlorocarbonyl)piperidine-1-carboxylate

生成物 1

HCID 595089554-(6-Chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester収率 97.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-chlorocarbonyl-piperidine-1-carboxylic acid benzyl ester (VII) (5.70 g, 20.2 mmol), 4-amino-6-chloropyrimidine (I) (2.10 g, 16.2 mmol) and 4-(N,N-dimethylamino)-pyridine (2.90 g, 23.7 mmol) in dichloromethane (50 ml) was heated to reflux temperature for 18 hours. The progress of the reaction was monitored by TLC, then dichloromethane was completely distilled off. Aqueous sodium bicarbonate solution was added to the residue and the mixture was extracted with ethyl acetate (3×100 ml). The organic layers were separated, dried over sodium sulfate and concentrated to obtain 4-(6-chloro-pyrimidin-4-ylcarbamoyl)-piperidine-1-carboxylic acid benzyl ester (VIII) (5.9 g, 79%) as a yellow solid.

後処理

  1. temperaturewas heated
  2. temperatureto reflux temperature for 18 hours
  3. distillationdichloromethane was completely distilled off
  4. additionAqueous sodium bicarbonate solution was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate (3×100 ml)
  6. customThe organic layers were separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-a2034e20e03a4e02a6575777a452b1ec
出典データセット
uspto-grants-2014_05
特許番号
US08716296B2

関連ノート

読み込み中…