Iodine → HCID 69431783, compound

HRID 854379Notes

Reaction equation

HRID 854379 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]2[C:15]3[N:16]=[CH:17][N:18]=[C:19]([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:14]=3[CH:13]=[CH:12]2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C([Li])CCC.[I:31]I>O1CCCC1.CCCCCC>[I:31][C:12]1[N:11]([S:8]([C:5]2[CH:4]=[CH:3][C:2]([CH3:1])=[CH:7][CH:6]=2)(=[O:9])=[O:10])[C:15]2[N:16]=[CH:17][N:18]=[C:19]([C:20]3[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=3)[C:14]=2[CH:13]=1

Participants

6

Reactant 3

HCID 807IodineHCID 69430099HCID 69430099, compoundHCID 178418339Butyllithium

Product 1

HCID 69431783HCID 69431783, compoundYield 19.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 7-[(4-methylphenyl)sulfonyl]4-pyridin-3-yl-7H-pyrrolo[2,3-d]pyrimidine [1 g, Reference Example 2] in tetrahydrofuran (20 mL) at −78° C. was added drop wise a solution of butyl lithium in hexane (2 mL, 1.6M) under inert atmosphere. The solution was stirred at that temperature for 1.5 hour and iodine (796 mg) was added. The reaction mixture was stirred at −78° C. for another 1 hour and allowed to reach room temperature. The reaction mixture was 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. 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 (260 mg) as an amorphous solid. MS: 477 [MH]+. LCMS (Method B) RT=3.26 minutes.

Workup

  1. stirringThe reaction mixture was stirred at −78° C. for another 1 hour
  2. customto reach room temperature
  3. customThe reaction mixture was partitioned between ethyl acetate and aqueous sodium sulfite solution
  4. customThe organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7a64eb763996428682d40548b5803431
Source dataset
uspto-grants-2007_08
Patent number
US07259154B2

Reaction notes

Loading…