Tripropylamine → 4-Amino-6-(3-cyclopentylpropionamido)quinazoline

HRID 1719929ノート

反応式

HRID 1719929 の反応式
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH2:13])[CH:11]=2)[N:6]=[CH:5][N:4]=1.C(N(CCC)CCC)CC.[CH:24]1([CH2:29][CH2:30][C:31](Cl)=[O:32])[CH2:28][CH2:27][CH2:26][CH2:25]1>N1C=CC=CC=1.C(OCC)(=O)C>[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([NH:13][C:31](=[O:32])[CH2:30][CH2:29][CH:24]3[CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:11]=2)[N:6]=[CH:5][N:4]=1

参加物

6

反応物 3

HCID 7616TripropylamineHCID 660393-Cyclopentylpropionyl chlorideHCID 202660864,6-Diaminoquinazoline hydrochloride

生成物 1

HCID 130604654-Amino-6-(3-cyclopentylpropionamido)quinazoline収率 49.8%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 4,6-diaminoquinazoline hydrochloride (10 g) and tripropylamine (26.4 g) in dry pyridine (100 ml) was stirred in an ice-bath for 20 minutes. To the mixture was added dropwise during 1.5 hours 3-cyclopentylpropionyl chloride (12.2 g). The mixture was stirred in an ice-bath for 1.5 hours. Crushed ice was added to the reaction mixture. The mixture was stirred for 5 minutes and concentrated under reduced pressure. After addition of water, sodium hydrogen carbonate was added in small portions to the mixture to give precipitates which were separated by filtration, washed with water and dried. The crude crystals were dissolved in a mixture of chloroform and methanol under heating. After the filtration of insoluble materials, the filtrate was treated with activated charcoal and concentrated under reduced pressure to give a residue. The residue was suspended in ethyl acetate. The suspension was stirred for 1 hour under heating and filtered to give crystalline 4-amino-6-(3-cyclopentylpropionamido)quinazoline (7.2 g).

後処理

  1. stirringThe mixture was stirred in an ice-bath for 1.5 hours
  2. additionCrushed ice was added to the reaction mixture
  3. stirringThe mixture was stirred for 5 minutes
  4. concentrationconcentrated under reduced pressure
  5. additionAfter addition of water, sodium hydrogen carbonate
  6. additionwas added in small portions to the mixture
  7. customto give
  8. customprecipitates which
  9. customwere separated by filtration
  10. washwashed with water
  11. customdried
  12. dissolutionThe crude crystals were dissolved in a mixture of chloroform and methanol
  13. temperatureunder heating
  14. filtrationAfter the filtration of insoluble materials
  15. additionthe filtrate was treated with activated charcoal
  16. concentrationconcentrated under reduced pressure
  17. customto give a residue
  18. stirringThe suspension was stirred for 1 hour
  19. temperatureunder heating
  20. filtrationfiltered

出典と根拠

ORDレコード
ord-95d93d81b667418da7291bd743abea94
出典データセット
uspto-grants-1985_09
特許番号
US04543356

反応ノート

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