2-[1-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one → 2-[1-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

HRID 570552Notes

Reaction equation

HRID 570552 reaction equation
[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[C:17](I)[C:18]3[C:23]([CH3:25])([CH3:24])[C:22](=[O:26])[NH:21][C:19]=3[N:20]=2)=[N:6]1>CN(C=O)C.[Pd]>[F:1][C:2]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:3]=1[CH2:4][N:5]1[C:9]2=[N:10][C:11]([CH3:14])=[N:12][CH:13]=[C:8]2[C:7]([C:15]2[N:16]=[CH:17][C:18]3[C:23]([CH3:25])([CH3:24])[C:22](=[O:26])[NH:21][C:19]=3[N:20]=2)=[N:6]1

Participants

4

Reactant 1

HCID 717466362-[1-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Product 1

HCID 717466392-[1-(2,3-Difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-oneYield 28.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

44 mg (0.05 mmol) of 2-[1-(2,3-difluorobenzyl)-6-methyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one were dissolved in 8 ml of absolute DMF, 11 mg (0.01 mmol) of 10% palladium on charcoal were added and hydrogenation was effected under standard hydrogen pressure for 4 h. The reaction mixture was filtered and purified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0). 6 mg of the target compound were obtained (purity 81%; 21% of theory).

Workup

  1. customfor 4 h
  2. filtrationThe reaction mixture was filtered
  3. custompurified by means of preparative HPLC (eluent: acetonitrile/water, gradient 20:80→100:0)

Sources & evidence

ORD record
ord-56e244ec3e6b477294df312249656dae
Source dataset
uspto-grants-2015_05
Patent number
US09023849B2

Reaction notes

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