Phenyl isocyanate → 3-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione

HRID 215688Notes

Reaction equation

HRID 215688 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[O:11][C:12](=O)[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][C:14]=1[NH2:19]>N1C=CC=CC=1>[C:1]1([N:7]2[C:12](=[O:11])[C:13]3[CH:18]=[CH:17][CH:16]=[N:15][C:14]=3[NH:19][C:8]2=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 351633Methyl 2-aminopyridine-3-carboxylate

Product 1

HCID 8201953-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dioneYield 61.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

17.22 g (144.6 mmol, 15.7 ml) phenylisocyanate was added to a suspenssion of 7.00 g (46.0 mmol) 2-aminonicotinic acid methyl ester in dry pyridine. The mixture was refluxed for 16 hours. The pyridine is was removed under reduced pressure and the residue was treated with 280 ml ethanol. The mixture is refluxed for 10 minutes. Upon cooling down 3-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione crystallized from the medium and was recrystallized from methoxypropanol. 6.73 g (61%) 3-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione was isolated (m.p. 304° C.).

Workup

  1. temperatureThe mixture was refluxed for 16 hours
  2. customThe pyridine is was removed under reduced pressure
  3. additionthe residue was treated with 280 ml ethanol
  4. temperatureThe mixture is refluxed for 10 minutes
  5. temperatureUpon cooling down 3-phenyl-1H-pyrido[2,3-d]pyrimidine-2,4-dione
  6. customcrystallized from the medium
  7. customwas recrystallized from methoxypropanol

Sources & evidence

ORD record
ord-a7fb018e00bd445d9c7fe8eb47e50dcb
Source dataset
uspto-grants-2012_06
Patent number
US08192918B2

Reaction notes

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