Sodium hydride → 7-Benzyloxy-4-(4-bromo-2,6-difluoroanilino)-6-methoxyquinazoline

HRID 346567

反応式

HRID 346567 の反応式
[H-].[Na+].[Br:3][C:4]1[CH:10]=[C:9]([F:11])[C:7]([NH2:8])=[C:6]([F:12])[CH:5]=1.[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25](Cl)=[N:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C>[CH2:13]([O:20][C:21]1[CH:30]=[C:29]2[C:24]([C:25]([NH:8][C:7]3[C:9]([F:11])=[CH:10][C:4]([Br:3])=[CH:5][C:6]=3[F:12])=[N:26][CH:27]=[N:28]2)=[CH:23][C:22]=1[O:32][CH3:33])[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 6101914-Bromo-2,6-difluoroanilineHCID 106619987-(Benzyloxy)-4-chloro-6-methoxyquinazoline

生成物 1

HCID 107906057-Benzyloxy-4-(4-bromo-2,6-difluoroanilino)-6-methoxyquinazoline収率 62.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (60%, 612 mg, 15.3 mmol) was added to a solution of 4-bromo-2,6-difluoroaniline (2.77 g, 6.65 mmol) in DMF (80 ml). After stirring for 30 minutes at ambient temperature, 7-benzyloxy-4-chloro-6-methoxyquinazoline (2 g, 6.65 mmol), (prepared, for example, as described in WO 97/22596, Example 1, but the free base was generated prior to use), was added and stirring was maintained for 4 hours. The mixture was partitioned between ethyl acetate and water (200 ml). The organic layer was separated, washed with water, brine, dried (MgSO4) and the volatiles were removed by evaporation. The residue was triturated with isopropanol, collected by filtration, washed with ether and dried under vacuum to give 7-benzyloxy-4-(4-bromo-2,6-difluoroanilino)-6-methoxyquinazoline (1.95 g, 62%).

後処理

  1. additionwas added
  2. stirringstirring
  3. temperaturewas maintained for 4 hours
  4. customThe mixture was partitioned between ethyl acetate and water (200 ml)
  5. customThe organic layer was separated
  6. washwashed with water, brine
  7. dry with materialdried (MgSO4)
  8. customthe volatiles were removed by evaporation
  9. customThe residue was triturated with isopropanol
  10. filtrationcollected by filtration
  11. washwashed with ether
  12. customdried under vacuum

出典と根拠

ORDレコード
ord-350db24fa5e547baa4985fd9b7d8d401
出典データセット
uspto-grants-2007_02
特許番号
US07173038B1

関連ノート

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