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Potassium Carbonate → 7-(2-(2-Bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline

HRID 2227970
ノート
印刷プレビュー

反応式

HRID 2227970 の反応式
Br[CH2:2][CH2:3][O:4][CH2:5][CH2:6][Br:7].[Cl:8][C:9]1[CH:28]=[CH:27][C:12]([NH:13][C:14]2[C:23]3[C:18](=[CH:19][C:20]([OH:26])=[C:21]([O:24][CH3:25])[CH:22]=3)[N:17]=[CH:16][N:15]=2)=[C:11]([F:29])[CH:10]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Br:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][O:26][C:20]1[CH:19]=[C:18]2[C:23]([C:14]([NH:13][C:12]3[CH:27]=[CH:28][C:9]([Cl:8])=[CH:10][C:11]=3[F:29])=[N:15][CH:16]=[N:17]2)=[CH:22][C:21]=1[O:24][CH3:25]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 21521Bis(2-bromoethyl) etherHCID 1355137204-(4-Chloro-2-fluorophenylamino)-7-hydroxy-6-methoxyquinazoline

生成物 1

HCID 187534287-(2-(2-Bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline収率 52.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

2-Bromoethyl ether (1.57 ml, 12 mmol) was added to a mixture of 4-(4-chloro-2-fluoroanilino)-7-hydroxy-6-methoxyquinazoline (1 g, 3.1 mmol), (prepared as described for the starting material in Example 2), and potassium carbonate (1.73 g, 12 mmol) in DMF (10 ml). The mixture was s for 18 hours at ambient temperature and was partitioned between ethyl acetate and water. The organic layer was separated, washed with water and then brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2). The purified product was triturated with ether, collected by filtration, washed with ether and dried under vacuum to give 7-(2-(2-bromoethoxy)ethoxy)-4-(4-chloro-2-fluoroanilino)-6-methoxyquinazoline (763 mg, 52%).

後処理

  1. custom(prepared
  2. customfor 18 hours
  3. customat ambient temperature
  4. customwas partitioned between ethyl acetate and water
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materialbrine, dried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by column chromatography on silica eluting with methylene chloride/acetonitrile/methanol (60/38/2)
  10. customThe purified product was triturated with ether
  11. filtrationcollected by filtration
  12. washwashed with ether
  13. customdried under vacuum

出典と根拠

ORDレコード
ord-a843b705108e42e6ba5c0ea4e7ef017c
出典データセット
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06414148B1

反応ノート

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