Dimethylformamide → HCID 13259452, compound

HRID 436405Notes

Reaction equation

HRID 436405 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][NH:10][C:9]2=[O:18])[CH:5]=[CH:6][CH:7]=1.CN(C)C=O.[H-].[Na+].[CH2:26](Br)[C:27]#[CH:28]>O>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:13]3[N:14]=[CH:15][CH:16]=[CH:17][C:12]=3[CH2:11][N:10]([CH2:28][C:27]#[CH:26])[C:9]2=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7842Propargyl bromideHCID 24758Sodium hydrideHCID 132593251-(3-Bromophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Product 1

HCID 13259452HCID 13259452, compoundYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 3.0 g of 1-(m-bromophenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 100 ml of dry dimethylformamide was added 0.6 g of 50% sodium hydride and the mixture was stirred for 30 minutes. To this was further added 3.5 g of propargyl bromide and the whole was reacted for one hour at room temperature. After the reaction was complete, the solvent was distilled off from the reaction mixture under reduced pressure. The residue thus obtained was diluted with water to release an oily product, which was then extracted with ether. The ether solution was dehydrated over magnesium sulfate, and separation and purification were accomplished by passing the solution through a column of alumina. The eluate thus obtained was concentrated to give 2.9 g of 1-(m-bromophenyl)-3-propargyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 118° - 119° C.

Workup

  1. customthe whole was reacted for one hour at room temperature
  2. distillationthe solvent was distilled off from the reaction mixture under reduced pressure
  3. customThe residue thus obtained
  4. extractionwas then extracted with ether
  5. customThe ether solution was dehydrated over magnesium sulfate, and separation and purification
  6. customThe eluate thus obtained
  7. concentrationwas concentrated

Sources & evidence

ORD record
ord-216fbba6c5f84e96a8509b85c5af267e
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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