Isopropyl iodide → 2-Chloro-9-isopropyl-6-(4-nitro-phenyl-amino)-9H-purine

HRID 9919

반응식

HRID 9919 반응식
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([N+:18]([O-:20])=[O:19])=[CH:14][CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH:27](I)([CH3:29])[CH3:28].O1CCOCC1>C(OCC)(=O)C.CN(C=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH:27]([CH3:29])[CH3:28])=[C:4]([NH:11][C:12]2[CH:13]=[CH:14][C:15]([N+:18]([O-:20])=[O:19])=[CH:16][CH:17]=2)[N:3]=1

참가 물질

8

반응물 4

HCID 6362Isopropyl iodideHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 219882602-Chloro-6-(4-nitro-phenyl-amino)-purine

생성물 1

HCID 219881912-Chloro-9-isopropyl-6-(4-nitro-phenyl-amino)-9H-purine

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture comprising 0.87 g (3 mmol) of 2-chloro-6-(4-nitro-phenyl-amino)-purine, 0.15 g (4.5 mmol) of caesium carbonate and 1.8 ml (18 mmol) of isopropyl iodide is stirred in 22 ml of a mixture comprising dioxane:water:DMF in a ratio of 2:1:4 at 100° C. for 48 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phase is washed with water and dried over sodium sulfate. After removal of the solvent, the residue is chromatographed over silica gel (mobile phase: CH2Cl2:methanol=9:1). The crystalline precipitate obtained on concentration is filtered off and dried. 2-Chloro-9-isopropyl-6-(4-nitro-phenyl-amino)-9H-purine is obtained; m.p.>260° C.; FAB-MS: (M+H)+=333; Rf=0.8 (CH2Cl2:methanol=9:1).

후처리

  1. washthe organic phase is washed with water
  2. dry with materialdried over sodium sulfate
  3. customAfter removal of the solvent
  4. customthe residue is chromatographed over silica gel (mobile phase: CH2Cl2:methanol=9:1)
  5. customThe crystalline precipitate obtained on concentration
  6. filtrationis filtered off
  7. customdried

출처 및 근거

ORD 기록
ord-11beb6d00d1b42dca5407a695e214e9e
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091346B1

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