Iodine → 4-Chloro-6-iodo-7-(4-methylbenzene-1-sulfonyl)-7H-pyrrolo[2,3-d]pyrimidine

HRID 854387Notes

Reaction equation

[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

Participants

Conditions

Temperature: -78 °C

Procedure

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.

Workup

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

Sources & evidence

ORD record: ord-802f0bb625ea464b9f9195ec5cc30e8d
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259154B2

Reaction notes

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