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-8-oxo-8,9-dihydro-7H-purine-6-carbonitrile

HRID 510116Notes

Reaction equation

HRID 510116 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.[Cu][C:31]#[N:32]>N1C=CC=CC=1>[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]([C:31]#[N:32])[N:15]=2)=[N:6]1

Participants

4

Reactant 2

HCID 867200522-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6-iodo-7-methyl-7,9-dihydro-8H-purin-8-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 569289472-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-7-methyl-8-oxo-8,9-dihydro-7H-purine-6-carbonitrileYield 19.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

200 mg (0.399 mmol) of the compound obtained in example 107 in pyridine (3 ml) were admixed with 37 mg (0.419 mmol) of copper(I) cyanide and heated to reflux overnight. After cooling, the reaction mixture was filtered and concentrated, and the residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient). 31 mg of the title compound were obtained (18% of theory).

Workup

  1. temperatureheated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. filtrationthe reaction mixture was filtered
  5. concentrationconcentrated
  6. customthe residue was purified by means of preparative HPLC (acetonitrile:water (+0.05% formic acid) gradient)

Sources & evidence

ORD record
ord-55e04695b06448b488c25828f6df0ad3
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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