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Dimethylformamide → 4-Amino-6-benzyloxy-2-chloro-7-methoxyquinazoline

HRID 2228489
ノート
印刷プレビュー

反応式

HRID 2228489 の反応式
CN(C)C=O.P(Cl)(Cl)([Cl:8])=O.[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:30][CH3:31])=[C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14](O)[N:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(C)C.C(OCC)(=O)C>[NH2:11][C:12]1[C:21]2[C:16](=[CH:17][C:18]([O:30][CH3:31])=[C:19]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH:20]=2)[N:15]=[C:14]([Cl:8])[N:13]=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

7

反応物 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178486884HCID 178486884、化合物

生成物 1

HCID 109799944-Amino-6-benzyloxy-2-chloro-7-methoxyquinazoline収率 27%

試薬・触媒・溶媒 2

HCID 3776Isopropanol
溶媒
HCID 8857Ethyl Acetate溶媒

反応条件

温度
90 °C

実験手順

N,N-Dimethyl formamide (7.9 ml, 0.10 mol) was added dropwise to phosphorus oxychloride (47.9 ml, 0.52 mol) with stirring. After 10 minutes, 4-amino-6-benzyloxy-2-hydroxy-7-methoxyquinazoline (16.4 g, 0.055 mol) was added portionwise and the resulting mixture heated at 90° C. for 1.5 hours, then cooled and poured into ethyl acetate (750 ml). The mixture was neutralised by the portionwise addition of aqueous sodium carbonate and the phases were separated. The organic layer was evaporated to dryness and the residue combined with the organic phase which was then treated with aqueous sodium hydroxide to basify (pH10) and the mixture was heated at 90° C. for 2 hours. After cooling, the mixture was partitioned between dichloromethane (11) and water (11), the organic phase washed with water, dried over MgSO4 and evaporated to give a pale yellow solid. Trituration with isopropanol afforded the subtitle compound as a colourless solid (4.64 g, 27%). Rf 0.64 (ethyl acetate:methanol 95:5, v/v). MS m/z 316, 318 (MH+).

後処理

  1. temperaturecooled
  2. customthe phases were separated
  3. customThe organic layer was evaporated to dryness
  4. additionwas then treated with aqueous sodium hydroxide
  5. temperaturethe mixture was heated at 90° C. for 2 hours
  6. temperatureAfter cooling
  7. customthe mixture was partitioned between dichloromethane (11) and water (11)
  8. washthe organic phase washed with water
  9. dry with materialdried over MgSO4
  10. customevaporated
  11. customto give a pale yellow solid

出典と根拠

ORDレコード
ord-a1aa1a0575e546f1b29a9aae380ac2ef
出典データセット
uspto-grants-2002_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06417194B1

反応ノート

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