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

HRID 1529174Notes

Reaction equation

HRID 1529174 reaction equation
[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([C:17]3[N:18]=[C:19](I)[C:20]4[C:25]([CH3:27])([CH3:26])[C:24](=[O:28])[NH:23][C:21]=4[N:22]=3)=[N:8]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[H][H]>CN(C=O)C.[Pd]>[CH:1]1([CH2:6][N:7]2[C:11]3=[N:12][CH:13]=[C:14]([F:16])[CH:15]=[C:10]3[C:9]([C:17]3[N:18]=[CH:19][C:20]4[C:25]([CH3:26])([CH3:27])[C:24](=[O:28])[NH:23][C:21]=4[N:22]=3)=[N:8]2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 2

HCID 867151712-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-4-iodo-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 714691492-[1-(Cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-3-yl]-5,5-dimethyl-5,7-dihydro-6H-pyrrolo[2,3-d]pyrimidin-6-one

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

230 mg (0.454 mmol) of 2-[1-(cyclopentylmethyl)-5-fluoro-1H-pyrazolo[3,4-b]pyridin-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, 150 mg of 10% palladium on carbon were added and the mixture was hydrogenated with hydrogen at standard pressure for 3 h. The reaction mixture was filtered through Celite and concentrated. The residue was triturated with 4 ml of acetonitrile, filtered off with suction and dried under high vacuum. This gave 123 mg of the target compound (purity 94%, 67% of theory).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated
  3. customThe residue was triturated with 4 ml of acetonitrile
  4. filtrationfiltered off with suction
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-9d0235c1b0bb475fa03d1c47bd16caae
Source dataset
uspto-grants-2015_07
Patent number
US09090610B2

Reaction notes

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