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

HRID 35839

반응식

HRID 35839 반응식
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

참가 물질

3

반응물 2

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

생성물 1

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

반응 조건

온도
170 °C

실험 절차

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.

후처리

  1. temperaturecooled

출처 및 근거

ORD 기록
ord-21a947e6faac44ebb55a92f9b1dcc4f3
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05411963

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