Iodine → 4-Iodo-6-propyl-pyrimidine-2-carbonitrile

HRID 733194Notes

Reaction equation

HRID 733194 reaction equation
[I:1]I.[CH2:3]([C:6]1[CH:11]=[C:10]([Sn](C)(C)C)[N:9]=[C:8]([C:16]#[N:17])[N:7]=1)[CH2:4][CH3:5]>C1COCC1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[I:1][C:10]1[CH:11]=[C:6]([CH2:3][CH2:4][CH3:5])[N:7]=[C:8]([C:16]#[N:17])[N:9]=1

Participants

5

Reactant 2

HCID 807IodineHCID 690493004-Propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile

Product 1

HCID 866196384-Iodo-6-propyl-pyrimidine-2-carbonitrileYield 72.1%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 24477Sodium ThiosulfateSolvent

Procedure

Iodine (1.64 g, 6.5 mmol) was added at room temperature to a solution of 4-propyl-6-trimethylstannanyl-pyrimidine-2-carbonitrile (2.0 g, 6.5 mmol) in THF (100 mL). The mixture was stirred at room temperature for 2 hours, then diluted with a saturated solution of sodium thiosulfate and the THF was removed under reduced pressure. The aqueous layer was extracted with ethyl acetate (3×100 ml). The combined organic layers were washed with brine, dried over sodium sulphate, filtered and concentrated under reduced pressure. The residue was chromatographed over silica gel (eluent:Cyclohexane/Ethyl acetate 5/5) to afford 4-iodo-6-propyl-pyrimidine-2-carbonitrile (1.28 g, 72%) as a colorless oil.

Workup

  1. customthe THF was removed under reduced pressure
  2. extractionThe aqueous layer was extracted with ethyl acetate (3×100 ml)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was chromatographed over silica gel (eluent:Cyclohexane/Ethyl acetate 5/5)

Sources & evidence

ORD record
ord-dfc5374f0c9a456a80635445dcc314c8
Source dataset
uspto-grants-2009_09
Patent number
US07589095B2

Reaction notes

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