2-Dimethylaminopyridine → 4-Pyren-1-yl-butyric acid 6-[4-(3-hexyl-ureido)-2-oxo-2H-pyrimidin-1-yl]-hexyl ester

HRID 658271

反応式

HRID 658271 の反応式
[C:1]1([CH2:17][CH2:18][CH2:19][C:20]([OH:22])=[O:21])[C:14]2[C:15]3=[C:16]4[C:11](=[CH:12][CH:13]=2)[CH:10]=[CH:9][CH:8]=[C:7]4[CH:6]=[CH:5][C:4]3=[CH:3][CH:2]=1.CN(C1C=CC=CN=1)C.[CH2:32]([NH:38][C:39]([NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53]O)[C:44](=[O:55])[N:43]=1)=[O:40])[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]>C(Cl)Cl>[CH2:32]([NH:38][C:39](=[O:40])[NH:41][C:42]1[CH:47]=[CH:46][N:45]([CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][O:21][C:20](=[O:22])[CH2:19][CH2:18][CH2:17][C:1]2[C:14]3[C:15]4=[C:16]5[C:11](=[CH:12][CH:13]=3)[CH:10]=[CH:9][CH:8]=[C:7]5[CH:6]=[CH:5][C:4]4=[CH:3][CH:2]=2)[C:44](=[O:55])[N:43]=1)[CH2:33][CH2:34][CH2:35][CH2:36][CH3:37]

参加物

5

反応物 3

HCID 218852-DimethylaminopyridineHCID 769771-Pyrenebutanoic acidHCID 689727261-Hexyl-3-[1-(6-hydroxy-hexyl)-2-oxo-1,2-dihydro-pyrimidinyl]-urea

生成物 1

HCID 866259794-Pyren-1-yl-butyric acid 6-[4-(3-hexyl-ureido)-2-oxo-2H-pyrimidin-1-yl]-hexyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of pyrene butyric acid (commercially available) (0.05 g, 0.17 mmol) in CH2Cl2 (5 ml) was added at 0° C., dicyclohexylcarboimide (0.044 g, 0.210 mmol) and dimethylaminopyridine (4 mg). The mixture was stirred for 1 h. 1-Hexyl-3-[1-(6-hydroxy-hexyl)-2-oxo-1,2-dihydro-pyrimidinyl]-urea) (J) was then added to the mixture and the solution was stirred at room temperature for 16 h. The solid was filtered off and the filtrate washed with water (2×10 ml) then saturated sodium chloride solution (5 ml). The organic phase was then dried (MgSO4) and the solvent evaporated in vacuo. The crude solid was purified using flash silica gel chromatography using a gradient: 1) (CHCl3) 2) (CHCl3/EtOAc, 5:1) and 3) (CHCl3/EtOAc/Et3N, 5:1:0.2). 4-Pyren-1-yl-butyric acid 6-[4-(3-hexyl-ureido)-2-oxo-2H-pyrimidin-1-yl]-hexyl ester (K) was obtained as a yellow solid (0.025 mg, 23%).

後処理

  1. stirringthe solution was stirred at room temperature for 16 h
  2. filtrationThe solid was filtered off
  3. washthe filtrate washed with water (2×10 ml)
  4. dry with materialThe organic phase was then dried (MgSO4)
  5. customthe solvent evaporated in vacuo
  6. customThe crude solid was purified

出典と根拠

ORDレコード
ord-ba111a3cf5044031ad59db91a39d0426
出典データセット
uspto-grants-2011_12
特許番号
US08076426B2

関連ノート

読み込み中…