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1-Naphthol → 6-Methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline

HRID 453988
ノート
印刷プレビュー

反応式

HRID 453988 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][CH2:17][N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].[C:30]1([OH:40])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1.[OH-].[Na+]>CN(C=O)C>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH2:15][CH2:16][CH2:17][N:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1)[N:5]=[CH:4][N:3]=[C:2]2[O:40][C:30]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][CH:31]=1
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

6

反応物 4

HCID 70051-NaphtholHCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazoline

生成物 1

HCID 220306666-Methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline収率 65%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
100 °C

実験手順

A mixture of 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (225 mg, 0.67 mmol), (prepared as described for the starting material in Example 1), potassium carbonate (106 mg, 0.77 mmol) and 1-naphthol (111 mg, 0.77 mmol) in DMF (7.5 ml) was stirred at 100° C. for 5 hours then allowed to cool to ambient temperature. The reaction mixture was treated with 1M aqueous sodium hydroxide solution (40 ml) and stirred at ambient temperature for a few minutes. The reaction mixture was extracted with ethyl acetate and the organic extracts were washed with water. The organic extracts were dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give a solid which was triturated with ether, filtered and dried to give 6-methoxy-7-(3-morpholinopropoxy)-4-(1-naphthyloxy)quinazoline (194 mg, 65%).

後処理

  1. custom(prepared
  2. temperatureto cool to ambient temperature
  3. stirringstirred at ambient temperature for a few minutes
  4. extractionThe reaction mixture was extracted with ethyl acetate
  5. washthe organic extracts were washed with water
  6. dry with materialThe organic extracts were dried (MgSO4)
  7. customthe solvent removed by evaporation
  8. customThe residue was purified by column chromatography
  9. washeluting with methylene chloride/methanol (95/5)
  10. customto give a solid which
  11. customwas triturated with ether
  12. filtrationfiltered
  13. customdried

出典と根拠

ORDレコード
ord-0a449045e1654ada8338b67ccbad41ec
出典データセット
uspto-grants-2013_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08492560B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート