Iodine → HCID 87073288, compound

HRID 76134Notes

Reaction equation

HRID 76134 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[CH:11][C:12](N)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.N(OC(C)(C)C)=O.[I:23]I>C(Cl)(Cl)(Cl)Cl>[I:23][C:12]1[CH:11]=[N:10][C:9]([C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 807IodineHCID 10906Tert-Butyl nitriteHCID 156743865-(4-Methoxyphenyl)pyrazin-2-amine

Product 1

HCID 87073288HCID 87073288, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
0 °C

Procedure

In a light protected flask, 4.10 g (20.4 mmol) 5-(4-methoxyphenyl)-pyrazin-2-amine are added to 140 mL carbon tetrachloride. After cooling down to 0° C. 4.12 mL (34.6 mmol) tert-butyl nitrite and 6.72 g (26.5 mmol) iodine are added sequently. Then cooling is removed and the reaction mixture is stirred at ambient temperature over night. The reaction mixture is diluted with DCM and washed sequently with aq. Na2S2O5 solution and water. The organic layer is dried with MgSO4 and the solvent is removed in vacuo. The residue is triturated with TBME and purified by column chromatography (silica gel, PE/EtOAc 6/4).

Workup

  1. temperatureThen cooling
  2. customis removed
  3. additionThe reaction mixture is diluted with DCM
  4. washwashed sequently with aq. Na2S2O5 solution and water
  5. dry with materialThe organic layer is dried with MgSO4
  6. customthe solvent is removed in vacuo
  7. customThe residue is triturated with TBME
  8. custompurified by column chromatography (silica gel, PE/EtOAc 6/4)

Sources & evidence

ORD record
ord-21d75c1bda0b448790fc29346dcf135d
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

Loading…