Water → 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

HRID 257786Notes

Reaction equation

HRID 257786 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:17]=[CH:18][CH:19]=1)[NH:7][C:8]1[C:13]([C:14](=[O:16])[NH2:15])=[CH:12][CH:11]=[CH:10][N:9]=1)([O-:3])=[O:2].[H-].[Na+].[C:22](N1C=CN=C1)(N1C=CN=C1)=[O:23].O>O1CCCC1.CCOC(C)=O.CCOCC>[N+:1]([C:4]1[CH:5]=[C:6]([N:7]2[C:8]3[N:9]=[CH:10][CH:11]=[CH:12][C:13]=3[C:14](=[O:16])[NH:15][C:22]2=[O:23])[CH:17]=[CH:18][CH:19]=1)([O-:3])=[O:2]

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 682631,1'-CarbonyldiimidazoleHCID 901913HCID 901913, compound

Product 1

HCID 127603011-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 54.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21584169Diethylether ethylacetateSolvent

Procedure

2-(3-Nitroanilino)-3-carbamoylpyridine (20 g, 77.5 mmole) was dissolved in tetrahydrofuran (2000 ml). Sodium hydride (60% dispersion in oil) (12.4 g, 310.0 mmole) was washed in hexanes and added to the solution. The solution was stirred for 5 minutes at room temperature under an inert atmosphere. To the solution, CDI (1,1'-carbonyldiimidazole) (18.8 g, 116.2 mmole) was added in a gradual manner over a period of 15 minutes, the resulting mixture was stirred at room temperature for 1 hour and subsequently refluxed for 24 hours. The solvent was removed resulting in a brown residue. Water was added to the residue and the resulting solution was extracted with ethyl acetate (5×300 ml). The phases were separated and the product was recrystallized from EtOAc/Et2O yielding a 12 g (42.4 mmole, 54.5% yield) of 1-N-(3-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (mp 262°-263° C.).

Workup

  1. additionadded to the solution
  2. stirringthe resulting mixture was stirred at room temperature for 1 hour
  3. temperaturesubsequently refluxed for 24 hours
  4. customThe solvent was removed
  5. customresulting in a brown residue
  6. extractionthe resulting solution was extracted with ethyl acetate (5×300 ml)
  7. customThe phases were separated

Sources & evidence

ORD record
ord-a4ee3e0e2c75403a8309eca7b015a5e2
Source dataset
uspto-grants-1993_11
Patent number
US05264437

Reaction notes

Loading…