HCID 178508327, compound → 2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine

HRID 1409104Notes

Reaction equation

HRID 1409104 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14](/[N:18]=N/C4C=CC=CC=4)=[C:13]([NH2:26])[N:12]=3)=[N:9][N:8]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[C:5]2=[N:6][CH:7]=1>CN(C=O)C.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[C:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:26])[N:12]=3)=[N:9][N:8]([CH2:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[F:34])[C:5]2=[N:6][CH:7]=1

Participants

4

Reactant 1

HCID 178508327HCID 178508327, compound

Product 1

HCID 580656032-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In DMF (800 ml), 39.23 g (85.75 mmol) of the compound from Example 10A were introduced and then 4 g of palladium (10% on carbon) were added. The mixture was hydrogenated with stirring overnight under standard hydrogen pressure. The batch was filtered over kieselguhr and the filter product was washed with a little DMF and then with a little methanol, and concentrated to dryness. The residue was admixed with ethyl acetate and stirred vigorously, and the precipitate was filtered off with suction, washed with ethyl acetate and diisopropyl ether and dried under a high vacuum over Sicapent.

Workup

  1. filtrationThe batch was filtered over kieselguhr
  2. washthe filter product was washed with a little DMF
  3. concentrationwith a little methanol, and concentrated to dryness
  4. stirringstirred vigorously
  5. filtrationthe precipitate was filtered off with suction
  6. washwashed with ethyl acetate and diisopropyl ether
  7. customdried under a high vacuum over Sicapent

Sources & evidence

ORD record
ord-5b7894ef380e453dbab1fd94614a2f52
Source dataset
uspto-grants-2014_12
Patent number
US08921377B2

Reaction notes

Loading…