Iodine → 5-Iodo-2-(piperazin-1-yl)pyrimidine

HRID 2120101Notes

Reaction equation

HRID 2120101 reaction equation
S(=O)(=O)(O)O.[N:6]1[CH:11]=[CH:10][CH:9]=[N:8][C:7]=1[N:12]1[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1.II.[I:20](O)(=O)(=O)=O>C(O)(=O)C.C(Cl)(Cl)Cl.O>[N:12]1([C:7]2[N:8]=[CH:9][C:10]([I:20])=[CH:11][N:6]=2)[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]1

Participants

8

Reactant 4

HCID 807IodineHCID 1118Sulfuric AcidHCID 65185Metaperiodic acidHCID 887471-(2-Pyrimidinyl)piperazine

Product 1

HCID 157298765-Iodo-2-(piperazin-1-yl)pyrimidine

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

In a mixture of acetic acid (5 ml), water (1 ml) and sulfuric acid (0.15 ml) was dissolved 2 g of 1-(2-pyrimidyl)piperazine which was then reacted with 0.86 g of iodine in the presence of 0.38 g of periodic acid at 100° C. for 6 hours with stirring. Chloroform was added to the reaction mixture, followed by washing with sodium hydrogen carbonate and brine. The organic layer thus obtained was dehydrated, filtered and concentrated under vacuum. Purification with column chromatography provided the title compound. 600 mg.

Workup

  1. washby washing with sodium hydrogen carbonate and brine
  2. customThe organic layer thus obtained
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. customPurification with column chromatography

Sources & evidence

ORD record
ord-8497e82d65084146bf261b70b4eee4d6
Source dataset
uspto-grants-2004_02
Patent number
US06689779B2

Reaction notes

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