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

HRID 1384533ノート

反応式

HRID 1384533 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%). 1H NMR Spectrum: (DMSOd6) 4.04(s, 3H); 5.47(s, 2H); 7.46(s, 1H); 7.50(d, 2H); 7.53(s, 1H); 8.60(d, 2H); 8.85(s, 1H) MS-ESI: 302 [MH]+

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-d851cbb2798b4250b82114a89e1634e4
出典データセット
uspto-grants-2001_07
特許番号
US06258951B1

反応ノート

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