4-Chloroquinazoline → 5-(2-Phenylethyl)-5-(4-quinazolyl) barbituric acid

HRID 35839

反応式

HRID 35839 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[CH:4][N:3]=1.[C:12]1([CH2:18][CH2:19][CH:20]2[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22][C:21]2=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>>[C:12]1([CH2:18][CH2:19][C:20]2([C:2]3[C:11]4[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=4)[N:5]=[CH:4][N:3]=3)[C:25](=[O:26])[NH:24][C:23](=[O:27])[NH:22][C:21]2=[O:28])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

参加物

3

反応物 2

HCID 788644-ChloroquinazolineHCID 231265045-(2-Phenylethyl) barbituric acid

生成物 1

HCID 542244535-(2-Phenylethyl)-5-(4-quinazolyl) barbituric acid

反応条件

温度
170 °C

実験手順

A mixture of 3.3 g of 4-chloroquinazoline and 4.65 g of 5-(2-phenylethyl) barbituric acid was heated to 170° C. for two and one-half hours, then cooled to form the 5-(2-phenylethyl)-5-(4-quinazolyl) barbituric acid. This compound was hydrolyzed, without isolation, by adding 40 ml of water and 4.5 g of NaOH to the mixture, heating to reflux for four hours. The mixture was cooled, acidified with HCl, refluxed two additional hours, then cooled, and neutralized. Product was extracted into CH2Cl2, which was then separated, dried, and evaporated. The residue was absorbed onto silica gel and eluted with 10% EtOAc/CH2Cl2 →20% EtOAc/CH2Cl2. Fractions containing product were combined. TLC showed impurities present. The product was rechromatographed using 15% EtOAc/CH2Cl2, however, impurities remained. Solvent was evaporated and the residue was redissolved in pentane. The product dissolved in pentane leaving impurities as a gummy residue. The pentane solution was decanted, filtered, and evaporated to give 0.75 g of the title product as a light oil.

後処理

  1. temperaturecooled

出典と根拠

ORDレコード
ord-21a947e6faac44ebb55a92f9b1dcc4f3
出典データセット
uspto-grants-1995_05
特許番号
US05411963

関連ノート

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