Sodium ethoxide → 8-Chloro-1-(3-{3-[(3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione

HRID 1097665ノート

反応式

HRID 1097665 の反応式
[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15]C(OCC)=O)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1.CC[O-].[Na+].[Cl:31][C:32]1[CH:33]=[C:34]([CH2:38]/[C:39](=[N:42]/[H])/[NH:40][OH:41])[CH:35]=[CH:36][CH:37]=1>CCO>[Cl:1][C:2]1[NH:10][C:9]2[C:8](=[O:11])[N:7]([CH2:12][CH2:13][CH2:14][C:15]3[O:41][N:40]=[C:39]([CH2:38][C:34]4[CH:35]=[CH:36][CH:37]=[C:32]([Cl:31])[CH:33]=4)[N:42]=3)[C:6](=[O:21])[N:5]([CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 2723922Sodium ethoxideHCID 66812467Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoateHCID 1785064602-(3-chlorophenyl)-N'-hydroxyethanimidamide

生成物 1

HCID 593957758-Chloro-1-(3-{3-[(3-chlorophenyl)methyl]-1,2,4-oxadiazol-5-yl}propyl)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione収率 49.3%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒2 回

反応条件

温度
140 °C

実験手順

Ethyl 5-(8-chloro-2,6-dioxo-3-pentyl-2,3,6,7-tetrahydro-1H-purin-1-yl)pentanoate (70 mg, 0.19 mmol) was dissolved in EtOH. The solution was treated with a 21% solution of NaOEt in EtOH (78 μl, 0.21 mmol) and (1Z)-2-(3-chlorophenyl)-N-hydroxyethanimidamide (38 mg, 0.21 mmol). The reaction was heated in the microwave at 140° C. for 10 min. The mixture was partitioned between EtOH and 2M HCl (aq). The organic layer was decanted off and concentrated. The crude product was purified on the MDAP. The product fractions were combined and concentrated to give the title compound as a white solid (46 mg, 49%).

後処理

  1. customThe mixture was partitioned between EtOH and 2M HCl (aq)
  2. customThe organic layer was decanted off
  3. concentrationconcentrated
  4. customThe crude product was purified on the MDAP
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-821438c68be944fb954e5c87a25d879e
出典データセット
uspto-grants-2012_03
特許番号
US08143264B2

反応ノート

読み込み中…