N,N-Dimethylaniline → 4-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline

HRID 279519ノート

反応式

HRID 279519 の反応式
O=P(Cl)(Cl)[Cl:3].[CH3:6][O:7][C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][C:17]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=1)[N:14]=[CH:13][NH:12][C:11]2=O.CN(C)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][C:11]1[C:10]2[C:15](=[CH:16][C:17]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[C:8]([O:7][CH3:6])[CH:9]=2)[N:14]=[CH:13][N:12]=1

参加物

5

反応物 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 135671184HCID 135671184、化合物

生成物 1

HCID 226249154-Chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline収率 41%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

Phosphorus oxytrichloride (0.1 ml) was added to a mixture of 6-methoxy-7-(4-pyridylmethoxy)-3,4-dihydroquinazolin-4-one (81 mg, 0.29 mmol) and N,N-dimethylaniline (0.1 ml) in toluene (5 ml), and the mixture heated at reflux for 1 hour. The volatiles were removed by evaporation and the residue partitioned between methylene chloride and aqueous ammonia. The organic extract was separated, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by chromatography on silica eluting with ethyl acetate progressing through increasingly polar mixtures to methanol/methylene chloride (1/9) to give 4-chloro-6-methoxy-7-(4-pyridylmethoxy)quinazoline (40 mg, 41%).

後処理

  1. temperaturethe mixture heated
  2. temperatureat reflux for 1 hour
  3. customThe volatiles were removed by evaporation
  4. customthe residue partitioned between methylene chloride and aqueous ammonia
  5. extractionThe organic extract
  6. customwas separated
  7. dry with materialdried (MgSO4)
  8. customthe solvent removed by evaporation
  9. customThe residue was purified by chromatography on silica eluting with ethyl acetate progressing
  10. temperaturethrough increasingly polar mixtures to methanol/methylene chloride (1/9)

出典と根拠

ORDレコード
ord-53968453313c4e5e8683beb8dcd02ce7
出典データセット
uspto-grants-2002_03
特許番号
US06362336B1

反応ノート

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