Water → 2-Chloro-5-(6,7-dimethoxyquinazolin-4-yloxy)aniline

HRID 871671

反応式

HRID 871671 の反応式
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].[C:10](=[O:13])([O-])[O-].[Cs+].[Cs+].Cl[C:17]1[N:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1.O.CN([CH:31]=[O:32])C>>[Cl:8][C:7]1[CH:6]=[CH:5][C:4]([O:9][C:25]2[C:24]3[C:19](=[CH:20][C:21]([O:13][CH3:10])=[C:22]([O:32][CH3:31])[CH:23]=3)[N:18]=[CH:17][N:26]=2)=[CH:3][C:2]=1[NH2:1]

参加物

6

反応物 5

HCID 962WaterHCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 740542-ChloroquinazolineHCID 50700783-Amino-4-chlorophenol

生成物 1

HCID 668763862-Chloro-5-(6,7-dimethoxyquinazolin-4-yloxy)aniline

実験手順

A solution of 3-amino-4-chlorophenol (1.00 g, 7.0 mmol) and cesium carbonate (3.38 g, 10.4 mmol) in DMF (20 mL) were heated at 80 C for 1 hr. The chloroquinazoline (1.61 g, 7.2 mmol) was added and the mixture heated for an additional hour. The mixture was poured into water (300 mL) and extracted with EtOAc twice. The combined extracts were washed with brine, dried with magnesium sulfate, filtered and concentrated. The residue was purified using silica gel chromatography eluting with EtOAc/hexane (30-70%), the main peak collected and triturated with DCM to afford 2-chloro-5-(6,7-dimethoxyquinazolin-4-yloxy)aniline. 1H NMR (300 MHz, DMSO d6) δ 3.96 (s, 6H), 5.55 (s, 2H), 6.45 (t, 1H), 6.76 (d, 1H), 7.25 (d, 1H), 7.36 (s, 1H), 7.50 (s, 1H), 8.55 (s, 1H); LC-MS (ESI) m/z 332 (M+H)+

後処理

  1. temperaturethe mixture heated for an additional hour
  2. extractionextracted with EtOAc twice
  3. washThe combined extracts were washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. washeluting with EtOAc/hexane (30-70%)
  9. customthe main peak collected
  10. customtriturated with DCM

出典と根拠

ORDレコード
ord-f6f03001d97f4108ba6db1cc0b1e2793
出典データセット
uspto-grants-2015_03
特許番号
US08969587B2

関連ノート

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