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

HRID 1287241Notes

Reaction equation

HRID 1287241 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].[H-].[Na+].[CH2:24](I)[CH:25]=[CH2:26].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]([CH2:26][CH:25]=[CH2:24])[C:11]2=[O:21])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11166Allyl iodideHCID 24758Sodium hydrideHCID 127603011-(m-nitrophenyl)pyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 127641811-(m-nitrophenyl)-3-allylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dioneYield 72%

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 the solution was added 0.6 g of approximately 50 % sodium hydride and stirring was performed for 30 minutes. To this was added 3.4 g of allyl iodide and the mixture was reacted for 3 hours at room temperature. Then the solvent was evaporated from the mixture under reduced pressure. To the residue obtained was added water to precipitate a crude product. Recrystallization of this product from methanol gave 2.3 g of 1-(m-nitrophenyl)-3-allylpyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione as pale yellow prisms, melting at 188-189°C.

Workup

  1. customthe mixture was reacted for 3 hours at room temperature
  2. customThen the solvent was evaporated from the mixture under reduced pressure
  3. customTo the residue obtained
  4. customto precipitate a crude product
  5. customRecrystallization of this product from methanol

Sources & evidence

ORD record
ord-dea5f694724e4ea6ae8c555e40e0ce5d
Source dataset
uspto-grants-1976_10
Patent number
US03984415

Reaction notes

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