Iodine chloride → HCID 178494242, compound

HRID 2354456Notes

Reaction equation

HRID 2354456 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.C(OCC)(=O)C.CO>[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

8

Reactant 4

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

Product 1

HCID 178494242HCID 178494242, compound

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

4-Methoxy-pyrazolo[3,4-d]pyrimidin-6-ylamine (6.75 g, 40.87 mmol) was suspended in an aqueous solution containing sodium acetate (6.0 g, 44.09 mmol) and iodine monochloride (9.12 g, 56.17 mmol) and stirred at 100° C. in a sealed reaction vessel for 24 h. The resulting mixture was cooled to room temperature and treated with a solution of sodium metabisulfite (3.6 g, 18.94 mmol) in 24 mL of water. The solid that formed was filtered, rinsed with water and dried: 6.93 g (58%) yield; TLC (10% methanol in ethyl acetate), Rf=0.57; 1H NMR (DMSO-d6) δ 13.08 (1H, br s, N−1 proton), 10.58 (1H, s, N−5 proton), 6.60 (2H, br s, 6-amino).

Workup

  1. temperatureThe resulting mixture was cooled to room temperature
  2. customThe solid that formed
  3. filtrationwas filtered
  4. washrinsed with water
  5. customdried
  6. custom6.93 g (58%) yield

Sources & evidence

ORD record
ord-238c28f491b04880b37149646a271fe8
Source dataset
uspto-grants-2010_07
Patent number
US07751982B2

Reaction notes

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