HCID 178418361, compound → 2-[5-fluoro-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]pyrimidine-4,5,6-triamine

HRID 510034Notes

Reaction equation

HRID 510034 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.[H][H]>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

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 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

39.23 g (85.75 mmol) of the compound from example 29A were initially charged in DMF (800 ml) and then 4 g of palladium (10% on charcoal) were added. Hydrogenation was effected at standard hydrogen pressure while stirring overnight. The mixture was filtered through kieselguhr, washed through with a little DMF and 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 mixture was filtered through kieselguhr
  2. washwashed through with a little DMF
  3. concentrationa 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-6ae247e202cf494f86fbb5d393c7e073
Source dataset
uspto-grants-2015_08
Patent number
US09096592B2

Reaction notes

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