Dimethylformamide → 3-Methyl-1-phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

HRID 436414Notes

Reaction equation

HRID 436414 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.[CH3:18]N(C)C=O.[H-].[Na+].P(OC)(OC)(OC)=O>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]([CH3:18])[C:8]2=[O:17])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10541Trimethyl PhosphateHCID 24758Sodium hydrideHCID 132592811-Phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 132593543-Methyl-1-phenyl-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.2 g of 1-phenyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 20 ml of dimethylformamide was added 0.5 g of approximately 50% sodium hydride, and the mixture was allowed to stand at room temperature for 30 minutes. To this was further added dropwise 4.2 g of trimethyl phosphate and the resulting mixture was heated at a temperature of 170° - 180° C in a sealed-tube for 7 hours. After the reaction was complete, the solvent was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was diluted with water, extracted with ether and dehydrated. The ether was removed by evaporation to leave a residue. This residue was recrystallized from a mixture of ether and petroleum ether to yield 1.7 g of 1-phenyl-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 172° - 173° C.

Workup

  1. temperaturethe resulting mixture was heated at a temperature of 170° - 180° C in a sealed-tube for 7 hours
  2. customthe solvent was removed from the reaction mixture by distillation under reduced pressure
  3. customThe residue thus obtained
  4. extractionextracted with ether
  5. customThe ether was removed by evaporation
  6. customto leave a residue
  7. customThis residue was recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-b7cac1341ee94d228b974287d6d4fcab
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

Loading…