Cesium carbonate → N-(2-(6-amino-8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl)-ethyl)-methanesulfonamide

HRID 527849

反応式

HRID 527849 の反応式
[I:1][C:2]1[C:3]([S:11][C:12]2[NH:13][C:14]3[C:19]([N:20]=2)=[C:18]([NH2:21])[N:17]=[CH:16][N:15]=3)=[CH:4][C:5]2[O:9][CH2:8][O:7][C:6]=2[CH:10]=1.Br[CH2:23][CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[NH2:21][C:18]1[N:17]=[CH:16][N:15]=[C:14]2[C:19]=1[N:20]=[C:12]([S:11][C:3]1[C:2]([I:1])=[CH:10][C:6]3[O:7][CH2:8][O:9][C:5]=3[CH:4]=1)[N:13]2[CH2:23][CH2:24][NH:25][S:26]([CH3:29])(=[O:28])=[O:27]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 285330N-(2-bromoethyl)methanesulfonamideHCID 178508697HCID 178508697、化合物

生成物 1

HCID 66554616N-(2-(6-amino-8-(6-iodo-benzo[1,3]dioxol-5-ylsulfanyl)-purin-9-yl)-ethyl)-methanesulfonamide収率 27.3%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
25 °C

実験手順

To a solution of 8-((6-iodobenzo[d][1,3]dioxol-5-yl)thio)-9H-purin-6-amine (100 mg, 0.24 mmol) in 5 mL of dry DMF was added N-(2-bromoethyl)methanesulfonamide (150 mg, 0.7 mmol) and Cs2CO3 (150 mg, 0.46 mmol). The resulting mixture was stirred at a temperature of about 25° C. for 3 hrs, condensed under reduced pressure and purified by flash chromatography to provide compound WS35 as white solid (35 mg, 27% yield).

後処理

  1. customcondensed under reduced pressure
  2. custompurified by flash chromatography

出典と根拠

ORDレコード
ord-180331ac5a5642bd9d365c396ac11e9e
出典データセット
uspto-grants-2016_05
特許番号
US09346808B2

関連ノート

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