Dimethylformamide → 1-Phenyl-3-isopropyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine

HRID 436409Notes

Reaction equation

HRID 436409 reaction equation
[C:1]1([N:7]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][NH:9][C:8]2=[O:17])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN(C)C=O.[H-].[Na+].[C:25]1(C)[CH:30]=CC(S(OC(C)C)(=O)=O)=C[CH:26]=1>O>[C:1]1([N:7]2[C:12]3[N:13]=[CH:14][CH:15]=[CH:16][C:11]=3[CH2:10][N:9]([CH:25]([CH3:30])[CH3:26])[C:8]2=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 598985Isopropyl tosylateHCID 132592811-Phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 132592871-Phenyl-3-isopropyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidineYield 256.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4.5 g of 1-phenyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 50 ml of dry dimethylformamide was added 1.2 g of 50% sodium hydride and the mixture was stirred for 30 minutes at room temperature, and then heated to a temperature of 90° - 100° C. To this was gradually added 1.28 g of isopropyl p-toluenesulfonate and the whole was reacted for 1 hour. After the reaction was complete, the solvent was distilled off from the mixture under reduced pressure. The residue obtained was diluted with water to produce a crude precipitate, which was collected by filtration and then dissolved in ethyl ether. Separation and purification were accomplished by applying the solution on a column of alumina, and the eluate was concentrated to give 4.1 g of 1-phenyl-3-isopropyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 164° - 165° C.

Workup

  1. temperatureheated to a temperature of 90° - 100° C
  2. customthe whole was reacted for 1 hour
  3. distillationthe solvent was distilled off from the mixture under reduced pressure
  4. customThe residue obtained
  5. customto produce a crude precipitate, which
  6. filtrationwas collected by filtration
  7. dissolutiondissolved in ethyl ether
  8. customSeparation and purification
  9. concentrationthe eluate was concentrated

Sources & evidence

ORD record
ord-78439cc78e74466f86901672c9df7715
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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