Iodine → 4-Chloro-6-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine

HRID 854387ノート

反応式

HRID 854387 の反応式
[Cl:1][C:2]1[C:3]2[CH:10]=[CH:9][N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1.C([Li])CCC.[I:26]I>O1CCCC1.CCCCCC>[Cl:1][C:2]1[C:3]2[CH:10]=[C:9]([I:26])[N:8]([S:11]([C:14]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[C:4]=2[N:5]=[CH:6][N:7]=1

参加物

6

反応物 3

HCID 807IodineHCID 442289674-Chloro-7-(p-toluenesulfonyl)-7H-pyrrolo[2,3-d]pyrimidineHCID 178418339Butyllithium

生成物 1

HCID 529112564-Chloro-6-iodo-7-tosyl-7H-pyrrolo[2,3-d]pyrimidine収率 20%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒

反応条件

温度
-78 °C

実験手順

To a solution of 4-chloro-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [5.4 g, Reference Example 3], in tetrahydrofuran (96 mL) at −78° C. was added drop wise a solution of butyl lithium in hexane (12.1 mL, 1.6M) under inert atmosphere. The solution was stirred at −78° C. for 3 hours and iodine (8.9 g) was added. The reaction mixture was stirred at −78° C. for 2 hours, and allowed to reach room temperature. The reaction mixture was partitioned between ethyl acetate and aqueous sodium sulfite solution, dried over magnesium sulfate and the solvent was evaporated under reduced pressure. The residue was subjected to flash column chromatography on silica eluting with a gradient of ethyl acetate and cyclohexane (50:50, to 100, v/v) to give the title compound (1.52 g) as an amorphous solid. MS: 434 [MH]+. LCMS (Method B) RT=4.26 minutes.

後処理

  1. stirringThe reaction mixture was stirred at −78° C. for 2 hours
  2. customto reach room temperature
  3. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium sulfite solution
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure

出典と根拠

ORDレコード
ord-802f0bb625ea464b9f9195ec5cc30e8d
出典データセット
uspto-grants-2007_08
特許番号
US07259154B2

反応ノート

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