Iodine → 6-iodo-4-methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine

HRID 854383Notes

Reaction equation

[CH3:1][O:2][C:3]1[C:4]2[CH:11]=[CH:10][N:9]([S:12]([C:15]3[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[C:5]=2[N:6]=[CH:7][N:8]=1.C([Li])CCC.[I:27]I>O1CCCC1.CCCCCC>[I:27][C:10]1[N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:13])=[O:14])[C:5]2[N:6]=[CH:7][N:8]=[C:3]([O:2][CH3:1])[C:4]=2[CH:11]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To a solution of 4-methoxy-7-[(4-methylphenyl)sulfonyl]-7H-pyrrolo[2,3-d]pyrimidine [2.23 g, Reference Example 7] in tetrahydrofuran (35 mL) at −78° C. was added drop wise a solution of butyl lithium in hexane (5 mL, 1.6M) under inert atmosphere. The solution was stirred at −70° C. for 1 hour and iodine (2.05 g) was added. The reaction mixture was stirred at −70° C. for another 1 hour, allowed to reach room temperature and partitioned between ethyl acetate and aqueous sodium sulfite solution. The organic phase was separated, then dried over magnesium sulfate and then evaporated under reduced pressure to give the title compound (2.64 g) as an amorphous solid. MS: 430 [MH]+. LCMS (Method B) RT=4.15 minutes.

Workup

stirringThe reaction mixture was stirred at −70° C. for another 1 hour
customto reach room temperature
custompartitioned between ethyl acetate and aqueous sodium sulfite solution
customThe organic phase was separated
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-770c36d41e3b451393dbb301fe610ee0
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07259154B2

Reaction notes

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