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Ammonium formate → 5-(4-Amino-2-fluorophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1260439
Notes
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Reaction equation

HRID 1260439 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]2[C:15]([NH:22][C:23]3[CH:28]=[CH:27][C:26]([N+:29]([O-])=O)=[CH:25][C:24]=3[F:32])=[C:16]([CH3:21])[C:17](=[O:20])[N:18]([CH3:19])[C:11]=2[N:10]=[CH:9]1)C1C=CC=CC=1.C([O-])=O.[NH4+]>O1CCOCC1.[OH-].[Pd+2].[OH-]>[NH2:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:15]2[C:12]3[C:13](=[O:14])[NH:8][CH:9]=[N:10][C:11]=3[N:18]([CH3:19])[C:17](=[O:20])[C:16]=2[CH3:21])=[C:24]([F:32])[CH:25]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 598230393-Benzyl-5-(2-fluoro-4-nitrophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 1360808875-(4-Amino-2-fluorophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 67.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst
HCID 31275
1,4-Dioxane
Solvent

Conditions

Temperature
60 °C

Procedure

3-Benzyl-5-(2-fluoro-4-nitrophenylamino)-6,8-dimethylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (4.1 mg, 9.42 mmol), palladium hydroxide (20% on carbon, 4 g) and ammonium formate (4 g, 63.4 mmol) were stirred in dioxane (200 mL) at 90° C. for 4 hours in a sealed pressure vessel. The suspension was filtered and the solid refluxed in DMF (20 mL) for 1 hour then filtered. This was repeated 3 times. The filtrates were combined and evaporated. The residue was dissolved in DMF (50 mL) and Quadrapure palladium scavenger (20 g) was added and the mixture stirred at 60° C. overnight. The mixture was filtered and evaporated, ether was added and a precipitate formed. This solid was filtered to give 2 g of the title compound (67%). [M+H] calc'd for C15H14FN5O2, 316. found, 316.

Workup

  1. filtrationThe suspension was filtered
  2. temperaturethe solid refluxed in DMF (20 mL) for 1 hour
  3. filtrationthen filtered
  4. customevaporated
  5. dissolutionThe residue was dissolved in DMF (50 mL)
  6. additionQuadrapure palladium scavenger (20 g) was added
  7. filtrationThe mixture was filtered
  8. customevaporated
  9. additionether was added
  10. customa precipitate formed
  11. filtrationThis solid was filtered

Sources & evidence

ORD record
ord-3060b5b2b18e48ddbece77a8b871b4eb
Source dataset
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08470837B2

Reaction notes

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