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

HRID 1260439Notes

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

Participants

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

filtrationThe suspension was filtered
temperaturethe solid refluxed in DMF (20 mL) for 1 hour
filtrationthen filtered
customevaporated
dissolutionThe residue was dissolved in DMF (50 mL)
additionQuadrapure palladium scavenger (20 g) was added
filtrationThe mixture was filtered
customevaporated
additionether was added
customa precipitate formed
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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