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Toluene → 6-Bromo-2-(4-tert-butyl-cyclohexyloxy)-quinazoline

HRID 525496
ノート
印刷プレビュー

反応式

HRID 525496 の反応式
C(=O)([O-])[O-].[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([OH:18])[N:12]=[CH:11]2.C(O)(C)(C)C.C1(C)C=CC=CC=1.CC(=O)CC.[C:36]([CH:40]1[CH2:45][CH2:44][CH:43](OS(C)(=O)=O)[CH2:42][CH2:41]1)([CH3:39])([CH3:38])[CH3:37]>>[Br:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]=[C:13]([O:18][CH:43]1[CH2:44][CH2:45][CH:40]([C:36]([CH3:39])([CH3:38])[CH3:37])[CH2:41][CH2:42]1)[N:12]=[CH:11]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 6

HCID 1140TolueneHCID 6386tert-ButanolHCID 6569Methyl Ethyl KetoneHCID 10796Cesium carbonateHCID 11128255Methanesulfonic acid 4-tert-butyl-cyclohexyl esterHCID 178517410HCID 178517410、化合物

生成物 1

HCID 68353046
6-Bromo-2-(4-tert-butyl-cyclohexyloxy)-quinazoline
収率 20%

反応条件

温度
110 °C

実験手順

Cesium carbonate (3.1308 g, 9.6089 mmol) was added to a mixture of 6-bromoquinazolin-2-ol (1.0812 g, 4.8044 mmol) in tert-butyl alcohol (15 mL, 160 mmol), toluene (25 mL, 230 mmol) and 2-butanone (10 mL, 100 mmol). The mixture was heated at 110° C. for 1 hour in a sealed tube then cooled to room temperature and methanesulfonic acid 4-tert-butyl-cyclohexyl ester (2.2519 g, 9.6089 mmol) was added. The reaction was then heated at 110° C. overnight. The reaction mixture was cooled to room temperature then filtered through a pad of celite. The filtrate was concentrated under reduced pressure, adsorbed onto silica gel and purified by flash chromatography (80 g SiO2 column; 0-40% EtOAc in heptane eluent) to give the title compound in 20% yield. ESI-MS (M+H+): 365.1

後処理

  1. temperaturethen cooled to room temperature
  2. temperatureThe reaction was then heated at 110° C. overnight
  3. temperatureThe reaction mixture was cooled to room temperature
  4. filtrationthen filtered through a pad of celite
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. custompurified by flash chromatography (80 g SiO2 column; 0-40% EtOAc in heptane eluent)

出典と根拠

ORDレコード
ord-af29dda143844841879cc7dc0f651244
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09340527B2

反応ノート

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