3-Chloroaniline → 2-chloro-N-(3-chlorophenyl)-9H-purin-6-amine

HRID 9895

反応式

HRID 9895 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([NH:14][CH:15]=[N:16]2)=[C:12](Cl)[N:11]=1>C(O)CCCC.C(O)(C)C>[Cl:9][C:10]1[N:18]=[C:17]2[C:13]([NH:14][CH:15]=[N:16]2)=[C:12]([NH:5][C:4]2[CH:6]=[CH:7][CH:8]=[C:2]([Cl:1])[CH:3]=2)[N:11]=1

参加物

5

反応物 2

HCID 79323-ChloroanilineHCID 53244122,6-Dichloropurine

生成物 1

HCID 219882322-chloro-N-(3-chlorophenyl)-9H-purin-6-amine

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 62761-Pentanol溶媒

反応条件

温度
100 °C

実験手順

1.4 ml (13 mmol) of 3-chloro-aniline are added to a suspension of 650 mg (3.44 mmol) of 2,6-dichloro-purine in 5 ml of 1-pentanol. The reaction mixture is stirred at 100° C. (oil bath temperature) for 3 hours. After cooling to room temperature, the mixture is diluted with isopropanol and stirred at 10° C. for 90 minutes. The precipitate is filtered off and rinsed with isopropanol and diethyl ether. The crystals are partitioned between 50 ml of 2 N (two normal) sodium hydroxide solution, 100 ml of water and 700 ml of ethyl acetate. The aqueous phase is subsequently extracted twice with ethyl acetate. The combined organic extracts are washed twice with water and once with saturated sodium chloride solution and dried over sodium sulfate. After filtration, the filtrate is concentrated under reduced pressure. The crude product is stirred with diethyl ether and the crystals are dried at 50° C. under an HV. 2-Chloro-6-(3-chloro-phenyl-amino)-purine is obtained; Rf=0.47 (ethyl acetate:hexane=3:1); APCI-MS: (M+H)+=280; HPLC: tret(grad 20/1)=10.26 minutes.

後処理

  1. temperatureAfter cooling to room temperature
  2. stirringstirred at 10° C. for 90 minutes
  3. filtrationThe precipitate is filtered off
  4. washrinsed with isopropanol and diethyl ether
  5. customThe crystals are partitioned between 50 ml of 2 N (two normal) sodium hydroxide solution, 100 ml of water and 700 ml of ethyl acetate
  6. extractionThe aqueous phase is subsequently extracted twice with ethyl acetate
  7. washThe combined organic extracts are washed twice with water and once with saturated sodium chloride solution
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration
  10. concentrationthe filtrate is concentrated under reduced pressure
  11. stirringThe crude product is stirred with diethyl ether
  12. customthe crystals are dried at 50° C. under an HV

出典と根拠

ORDレコード
ord-cf753584cff448f29f411f9c50bea731
出典データセット
uspto-grants-2006_08
特許番号
US07091346B1

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