HCID 67271440, compound → HCID 58851321, compound

HRID 1696443Notes

Reaction equation

HRID 1696443 reaction equation
[CH3:1][N:2]1[C:7]2[N:8]=[CH:9][N:10]=[CH:11][C:6]=2[CH:5]=[C:4]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=O)[CH:13]=2)[C:3]1=[O:21]>CCO.[Pd]>[NH2:18][C:14]1[CH:13]=[C:12]([C:4]2[C:3](=[O:21])[N:2]([CH3:1])[C:7]3[N:8]=[CH:9][N:10]=[CH:11][C:6]=3[CH:5]=2)[CH:17]=[CH:16][CH:15]=1

Participants

4

Reactant 1

HCID 67271440HCID 67271440, compound

Product 1

HCID 58851321HCID 58851321, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 8-methyl-6-(3-nitrophenyl)-8H-pyrido[2,3-d]pyrimidin-7-one (0.35 g, 1.2 mmol) in EtOH (10 mL) was added Pd (0.2 g). The mixture was stirred under an atmosphere of H2 (30 psi) for 1.5 h. After removal of the catalyst by filtration, the solvent was evaporated under vacuum to give 6-(3-aminophenyl)-8-methyl-8H-pyrido[2,3-d]pyrimidin-7-one (150 mg, 50% yield) as a white solid. 1H NMR (300 MHz, DMSO-d6): δ 9.08 (d, J=4.2 Hz, 1H), 8.18 (s, 1H), 7.85 (m, 1H), 7.80 (d, J=5.4 Hz, 1H), 7.64 (t, J=7.8 Hz, 1H), 7.43 (d, J=5.4 Hz, 1H), 3.85 (s, 3H).

Workup

  1. customAfter removal of the catalyst
  2. filtrationby filtration
  3. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-8c7d4b4f4ad84be8a8115fecb660a426
Source dataset
uspto-grants-2012_04
Patent number
US08163756B2

Reaction notes

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