Ammonium formate → 5-((4-Amino-2-fluorophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

HRID 1660879Notes

Reaction equation

HRID 1660879 reaction equation
C([N:8]1[C:13](=[O:14])[C:12]2[C:15]([NH:21][C:22]3[CH:27]=[CH:26][C:25]([N+:28]([O-])=O)=[CH:24][C:23]=3[F:31])=[CH:16][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-]>[NH2:28][C:25]1[CH:26]=[CH:27][C:22]([NH:21][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])[CH:16]=2)=[C:23]([F:31])[CH:24]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 598230443-Benzyl-5-((2-fluoro-4-nitrophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione

Product 1

HCID 1357416545-((4-Amino-2-fluorophenyl)amino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dioneYield 66.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 312751,4-DioxaneSolvent

Procedure

3-Benzyl-5-(2-fluoro-4-nitrophenylamino)-8-methylpyrido[2,3-d]pyrimidine-4,7(3H,8H)-dione (900 mg, 2.1 mmol), palladium hydroxide (20% on carbon, 500 mg) and ammonium formate (500 mg, 7.93 mmol, 3.7 eq) were stirred in dioxane (10 mL) at 90° C. for 4 hours. 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 to give 420 mg of title compound as a white solid (65%). 1H NMR (400 MHz, MeOD) δ ppm 3.56 (br. s., 3H) 5.38 (s, 1H) 6.51 (s, 1H) 6.54 (t, J=1.89 Hz, 1H) 7.07 (t, J=8.46 Hz, 1H) 8.17 (s, 1H) [M+H] calc'd for C14H12FN5O2, 302; found, 302.

Workup

  1. filtrationThe suspension was filtered
  2. temperaturethe solid refluxed in DMF (20 mL) for 1 hour
  3. filtrationthen filtered
  4. customevaporated

Sources & evidence

ORD record
ord-1e0c180351624cf5917041114075027f
Source dataset
uspto-grants-2011_10
Patent number
US08030317B2

Reaction notes

Loading…