1,4-Diiodobutane → 2-(4-(Pyrimidin-2-ylthio)butylthio)pyrimidine

HRID 2103945Notes

Reaction equation

HRID 2103945 reaction equation
[SH:1][C:2]1[N:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[CH2:8](O[K])[CH3:9].I[CH2:13][CH2:14][CH2:15][CH2:16]I>C(O)C>[N:3]1[CH:4]=[CH:5][CH:6]=[N:7][C:2]=1[S:1][CH2:13][CH2:14][CH2:15][CH2:16][S:1][C:2]1[N:7]=[CH:9][CH:8]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 123371,4-DiiodobutaneHCID 178418793HCID 178418793, compoundHCID 178473702HCID 178473702, compound

Product 1

HCID 578047232-(4-(Pyrimidin-2-ylthio)butylthio)pyrimidineYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

20 mmole of 2-mercaptopyrimidine was dissolved in 20 ml of ethanol with stirring. 20 mole of EtOK (24 weight % in ethanol) was added to the solution, stirred for 5 minutes. Then, about 10 mmole of 1,4-diiodobutane was added, and stirred overnight. The white precipitate was removed by filtration, the solvent in the filtrate was removed in vacuum. The obtained solid was dissolved in CH2Cl2, and separated with a Si gel column (solvents: 1 ethylacetate/1 hexane in volume). Yield: 86%. 1H NMR (CDCl3) of PyrC4: δ(ppm) 8.50 (4H, d, JH-H=4.77), 6.94 (2H, t, JH-H=4.77), 3.20 (4H, t, JH-H=6.93), and 1.91 (4H, t, JH-H=6.93).

Workup

  1. stirringstirred for 5 minutes
  2. stirringstirred overnight
  3. customThe white precipitate was removed by filtration
  4. customthe solvent in the filtrate was removed in vacuum
  5. dissolutionThe obtained solid was dissolved in CH2Cl2
  6. customseparated with a Si gel column (solvents: 1 ethylacetate/1 hexane in volume)

Sources & evidence

ORD record
ord-323fed9735a84769a9e34cba80197fb7
Source dataset
uspto-grants-2009_08
Patent number
US07576165B2

Reaction notes

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