Water → HCID 178508263, compound

HRID 334398Notes

Reaction equation

HRID 334398 reaction equation
O.[NH2:2][NH2:3].[NH2:4][C:5]1[C:12]([I:13])=[CH:11][C:8]([C:9]#[N:10])=[C:7](S(C)=O)[N:6]=1.O>CC(O)C>[I:13][C:12]1[CH:11]=[C:8]2[C:9]([NH2:10])=[N:3][NH:2][C:7]2=[N:6][C:5]=1[NH2:4]

Participants

5

Reactant 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 682764766-Amino-5-iodo-2-(methylsulfinyl)nicotinonitrile

Product 1

HCID 178508263HCID 178508263, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
80 °C

Procedure

275 μl (2 eq) of hydrazine monohydrate is added to a solution of 872 mg (2.84 mmol) of 6-amino-5-iodo-2-(methylsulfinyl)nicotinonitrile in 11 ml of 2-propanol. The reaction medium is stirred at 80° C. for 3 hours. Water is added and the product is extracted with ethyl acetate. The organic phase is dried on magnesium sulfate, filtered and evaporated. The residue is triturated in a minimum of diisopropyl ether. The solid is filtered to yield 523 mg (67%) of 5-iodo-1H-pyrazolo[3,4-b]pyridin-3,6-diamine in the form of a brown powder.

Workup

  1. extractionthe product is extracted with ethyl acetate
  2. customThe organic phase is dried on magnesium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customThe residue is triturated in a minimum of diisopropyl ether
  6. filtrationThe solid is filtered

Sources & evidence

ORD record
ord-6ad15c8dbc824cf48d9db557bd69a2f0
Source dataset
uspto-grants-2014_11
Patent number
US08883821B2

Reaction notes

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