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Potassium Carbonate → N9-(3-Chloropropyl)-2-amino-6-chloropurine

HRID 1695084
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HRID 1695084 반응식
[Cl:1][C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.C([O-])([O-])=O.[K+].[K+].C[N:18](C=O)C.Br[CH2:23][CH2:24][CH2:25][Cl:26]>O>[Cl:26][CH2:25][CH2:24][CH2:23][N:6]1[CH:5]=[N:4][C:3]2[C:7]1=[N:8][C:9]([NH2:18])=[N:10][C:2]=2[Cl:1]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 53592776-ChloropurineHCID 86615609DMF 1-bromo-3-chloropropane

생성물 1

HCID 85823850N9-(3-Chloropropyl)-2-amino-6-chloropurine수율 36.1%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
50 °C

실험 절차

To a stirred suspension of 6-chloropurine (5.0 g, 29.48 mmol) and K2CO3 (4.48 g, 32.42 mmol) in dry DMF 1-bromo-3-chloropropane (13.92 g, 88.45 mmol) is added. The reaction mixture is heated to 50° C. for 1 min and stirred at room temperature for additional 3 h. The reaction mixture is poured into 120 mL of water and extracted with CH2Cl2. The combined organic phases are washed with water, dried over MgSO4 and evaporated in vacuo. The residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1) to yield 2.6 g (10.65 mmol, 35%) of the title compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6): δ=8.11 (s, 1H, H-8), 6.91 (s, 2H, NH2), 4.16 (t, J=6.8, 2H, CH2), 3.63 (t, J=6.8, 2H CH2), 2.25 (m, 2H, CH2) ppm. MS (ESI) m/z 247.3 [M+H]+.

후처리

  1. additionis added
  2. extractionextracted with CH2Cl2
  3. washThe combined organic phases are washed with water
  4. dry with materialdried over MgSO4
  5. customevaporated in vacuo
  6. customThe residue is purified by flash column chromatography (dichloromethane/methanol 50:1 to 10:1)

출처 및 근거

ORD 기록
ord-25928c8fa6354b1ca2f91a0da09e53cb
출처 데이터셋
uspto-grants-2012_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08163479B2

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