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1-溴-3-氯丙烷 → 9-(3-Chloropropyl)-2-butoxy-8-methoxy-9H-purin-6-amine

HRID 527770
笔记
打印预览

反应方程式

HRID 527770 反应方程式
FC(F)(F)C(O)=O.[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11].C(=O)([O-])[O-].[K+].[K+].Br[CH2:32][CH2:33][CH2:34][Cl:35]>CN(C=O)C>[CH2:8]([O:12][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:32][CH2:33][CH2:34][Cl:35])=[C:15]([NH2:24])[N:14]=1)[CH2:9][CH2:10][CH3:11]
参与物反应条件实验过程后处理来源与证据反应笔记

参与物

5

反应物 3

HCID 80061-溴-3-氯丙烷HCID 11430碳酸钾HCID 178450370HCID 178450370,化合物

产物 1

HCID 592526379-(3-Chloropropyl)-2-butoxy-8-methoxy-9H-purin-6-amine收率 70%

试剂、催化剂与溶剂 1

HCID 6228N,N-二甲基甲酰胺溶剂

反应条件

温度
50 °C

实验过程

2-(Butyloxy)-8-(methyloxy)-9H-purin-6-amine trifluoroacetate (4.7 g, 13.38 mmol) and potassium carbonate (4.62 g, 33.4 mmol) in dry DMF (50 ml) were stirred and heated at 50° C., under nitrogen, for 75 mins. The mixture was allowed to cool to room temperature and then cooled to 0° C. and 1-bromo-3-chloropropane (2.106 g, 13.38 mmol) was added. The mixture was stirred at 0 to 10° C. for approximately 5 hours then allowed to warm to room temperature and stirred for approximately a further 40 hours when LCMS indicated approximately 70% of the desired product. The mixture was allowed to settle and the supernatant was pipetted off and the solvent evaporated on a rotary evaporator using a high vacuum pump at about 23° C. Chloroform and water was added to the combined residues which were stirred and the phases separated using a hydrophobic frit. The aqueous layer was re-extracted with further portions of chloroform and the combined chloroform extracts were evaporated under high vacuum at 23° C. to give a yellow solid (2.798 g). This crude material was combined with similar material obtained from two similar preparations (0.56 g and 0.995 g) and purified by flash column chromatography on silica using 2:1 ethyl acetate/chloroform as eluant to give the title compound as an off-white solid. (3.011 g).

后处理

  1. temperatureto cool to room temperature
  2. temperaturecooled to 0° C.
  3. temperatureto warm to room temperature
  4. stirringstirred for approximately a further 40 hours when LCMS

来源与证据

ORD记录
ord-b6f18bbf623e47cb82c016d838e0c22a
来源数据集
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
专利号
US09346806B2

反应笔记

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本页导航参与物反应条件实验过程后处理来源与证据反应笔记