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Potassium Carbonate → 4-(Chloro-2-fluoroanilino)-6-methoxy-7-(3-tetrahydropyran-2-yloxypropoxy)quinazoline

HRID 1838556
ノート
印刷プレビュー

反応式

HRID 1838556 の反応式
[Cl:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([OH:22])=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9].Br[CH2:24][CH2:25][CH2:26][O:27][CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[Cl:1][N:2]([C:10]1[C:19]2[C:14](=[CH:15][C:16]([O:22][CH2:24][CH2:25][CH2:26][O:27][CH:28]3[CH2:33][CH2:32][CH2:31][CH2:30][O:29]3)=[C:17]([O:20][CH3:21])[CH:18]=2)[N:13]=[CH:12][N:11]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[F:9]
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 3

HCID 11430Potassium CarbonateHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 1359906824-(Chloro-2-fluoroanilino)7-hydroxy-6-methoxyquinazoline

生成物 1

HCID 187534244-(Chloro-2-fluoroanilino)-6-methoxy-7-(3-tetrahydropyran-2-yloxypropoxy)quinazoline収率 49%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6228
Dimethylformamide
溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-(chloro-2-fluoroanilino)-7-hydroxy-6methoxyquinazoline (3.28 g, 10 mmol), (prepared as described for the starting material in Example 2), 1-bromo-3-tetrahydropyranyloxypropane (2.5 g, 11 mmol) and potassium carbonate (5.0 g, 36 mmol) in DMF (50 ml) was stirred and heated at 90° C. for 3 hours. The reaction mixture was allowed to cool, was diluted with water (500 ml) and extracted with ethyl acetate (3×100 ml). The extracts were combined, washed with water (×3), and then brine, and dried (MgSO4). The solvent was removed by evaporation and the residue was purified by column chromatography eluting with ethyl acetate. The purified product was recrystallised from ethyl acetate/hexane to give 4-(chloro-2-fluoroanilino)-6-methoxy-7-(3-tetrahydropyran-2-yloxypropoxy)quinazoline (2.25 g, 49%).

後処理

  1. custom(prepared
  2. temperatureto cool
  3. extractionextracted with ethyl acetate (3×100 ml)
  4. washwashed with water (×3)
  5. dry with materialbrine, and dried (MgSO4)
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by column chromatography
  8. washeluting with ethyl acetate
  9. customThe purified product was recrystallised from ethyl acetate/hexane

出典と根拠

ORDレコード
ord-94d57815a11644cca9583229f44eadfa
出典データセット
uspto-grants-2004_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06673803B2

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