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2-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamine → 2-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine

HRID 1528677
Notes
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Reaction equation

HRID 1528677 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([N+:18]([O-])=O)=[C:13]([NH2:21])[N:12]=3)[N:9]=[C:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:5]2=[N:6][CH:7]=1.[H][H]>N1C=CC=CC=1.[Pd]>[F:1][C:2]1[CH:3]=[C:4]2[N:10]([C:11]3[N:16]=[C:15]([NH2:17])[C:14]([NH2:18])=[C:13]([NH2:21])[N:12]=3)[N:9]=[C:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[F:29])[C:5]2=[N:6][CH:7]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 675169662-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]-5-nitropyrimidine-4,6-diamineHCID 178418361HCID 178418361, compound

Product 1

HCID 675168882-[6-Fluoro-3-(2-fluorobenzyl)-1H-pyrazolo[4,3-b]pyridin-1-yl]pyrimidine-4,5,6-triamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 1049
Pyridine
Solvent

Procedure

196 mg (0.492 mmol) of the compound from example 7A were initially charged in pyridine (22 ml), 74 mg of palladium on carbon (10% by weight) were then added and the mixture was hydrogenated at standard hydrogen pressure overnight. The reaction mixture was then filtered through kieselguhr, the filter cake was washed with ethanol and the filtrate was concentrated. The residue was triturated with ethanol at 50° C., and the solid was filtered off and dried under high vacuum. This gave 107 mg (58% of theory) of the title compound.

Workup

  1. filtrationThe reaction mixture was then filtered through kieselguhr
  2. washthe filter cake was washed with ethanol
  3. concentrationthe filtrate was concentrated
  4. customThe residue was triturated with ethanol at 50° C.
  5. filtrationthe solid was filtered off
  6. customdried under high vacuum

Sources & evidence

ORD record
ord-d2a48d63c4e544c1a8b6404cfb81556a
Source dataset
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09090609B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes