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

HRID 854387노트

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HRID 854387 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

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온도
-78 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-802f0bb625ea464b9f9195ec5cc30e8d
출처 데이터셋
uspto-grants-2007_08
특허 번호
US07259154B2

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