2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-iodo-7-methyl-7,9-dihydro-8H-purin-8-one → 2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-methyl-7,9-dihydro-8H-purin-8-one

HRID 510131Notes

Reaction equation

HRID 510131 reaction equation
[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:22]=[C:21]3[C:17]([N:18]([CH3:24])[C:19](=[O:23])[NH:20]3)=[C:16](I)[N:15]=2)=[N:6]1>CN(C)C=O.[Pd]>[F:1][C:2]1[CH:29]=[CH:28][CH:27]=[CH:26][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][CH:13]=[C:8]2[C:7]([C:14]2[N:22]=[C:21]3[C:17]([N:18]([CH3:24])[C:19](=[O:23])[NH:20]3)=[CH:16][N:15]=2)=[N:6]1

Participants

4

Reactant 1

HCID 867200522-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-iodo-7-methyl-7,9-dihydro-8H-purin-8-one

Product 1

HCID 666143252-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-methyl-7,9-dihydro-8H-purin-8-oneYield 78.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

Under an argon atmosphere, 225 mg (approx. 0.112 mmol) of the compound from example 107 were dissolved in 15 ml of dimethylformamide, admixed with 150 mg of 10% palladium on charcoal and hydrogenated under standard hydrogen pressure overnight. The reaction mixture was filtered through Celite and concentrated, and the residue was purified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 60:35:5→35:60:5). 33 mg of the title compound were obtained (76% of theory).

Workup

  1. custompressure overnight
  2. filtrationThe reaction mixture was filtered through Celite
  3. concentrationconcentrated
  4. customthe residue was purified by means of preparative HPLC (eluent: water/acetonitrile/water with 1% trifluoroacetic acid, gradient 60:35:5→35:60:5)

Sources & evidence

ORD record
ord-9e419cdd57814f9d90688065a876203d
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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