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

HRID 1287243Notes

Reaction equation

HRID 1287243 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[NH:12][C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].P(OC)(OC)(O[CH3:25])=O.O>CN(C)C=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:15]3[N:16]=[CH:17][CH:18]=[CH:19][C:14]=3[C:13](=[O:20])[N:12]([CH3:25])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 10541Trimethyl PhosphateHCID 127603011-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 127641771-(m-nitrophenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 85.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.8 g of 1-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione was dissolved in 30 ml of dry dimethylformamide. To this was added 4.2 g of trimethyl phosphate and the mixture was refluxed for 6 hours. After the reaction was complete, the solvent was distilled off from the mixture, and to the residue obtained was added water to precipitate a crude product. The product was recrystallized from acetone to yield 2.5 g of 1-(m-nitrophenyl)-3-methylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 234°-235°C.

Workup

  1. temperaturethe mixture was refluxed for 6 hours
  2. distillationthe solvent was distilled off from the mixture
  3. customto the residue obtained
  4. customto precipitate a crude product
  5. customThe product was recrystallized from acetone

Sources & evidence

ORD record
ord-98fd3106419240658e4f14d195597ec4
Source dataset
uspto-grants-1976_10
Patent number
US03984415

Reaction notes

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