Iodine chloride → HCID 178494242, compound

HRID 1062820Notes

Reaction equation

HRID 1062820 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([NH2:9])[N:6]=[C:5]2[NH:10][N:11]=[CH:12][C:4]=12.C([O-])(=O)C.[Na+].[I:18]Cl.S(S([O-])=O)([O-])(=O)=O.[Na+].[Na+]>O>[I:18][C:12]1[C:4]2[C:5](=[N:6][C:7]([NH2:9])=[N:8][C:3]=2[O:2][CH3:1])[NH:10][N:11]=1

Participants

6

Reactant 4

HCID 24640Iodine chlorideHCID 517045Sodium AcetateHCID 656671Sodium PyrosulfiteHCID 112521974-Methoxy-1H-pyrazolo[3,4-d]pyrimidin-6-amine

Product 1

HCID 178494242HCID 178494242, compoundYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of compound 4 (105 g, 0.636 mol), sodium acetate (263 g) and iodine monochloride (140 g) was mechanically stirred in 1.3 L of water at a temperature between 92-98° C. for 5 h. The mixture was cooled to room temperature and a solution of sodium metabisulfite (139 g in 500 ml of water) was added. The mixture was stirred for 10 minutes and then filtered. The solid was rinsed with water and dried. The resulting dried solid was dissolved in 840 ml of hot DMF and precipitate by addition of 800 ml of water. The mixture was cooled in an ice-bath and the solid was filtered and dried to provide 144 g (78% yield) of 3-iodo-4-methoxy-6-aminopyrazolo[3,4-d]pyrimidine (5).

Workup

  1. filtrationfiltered
  2. washThe solid was rinsed with water
  3. customdried
  4. customThe resulting dried solid
  5. dissolutionwas dissolved in 840 ml of hot DMF
  6. additionprecipitate by addition of 800 ml of water
  7. temperatureThe mixture was cooled in an ice-bath
  8. filtrationthe solid was filtered
  9. customdried

Sources & evidence

ORD record
ord-6979ae1963834190b21c9e89590d9238
Source dataset
uspto-grants-2005_11
Patent number
US06962991B2

Reaction notes

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