Dimethylformamide → HCID 13259295, compound

HRID 436413Notes

Reaction equation

HRID 436413 reaction equation
[Cl: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.[CH3:19]N(C)C=O.[H-].[Na+].FCOS([O-])(=O)=O>O>[Cl: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]([CH3:19])[C:9]2=[O:18])[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 132592941-(3-Chlorophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-oneHCID 21452456HCID 21452456, compound

Product 1

HCID 13259295HCID 13259295, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 2.6 g of 1-(m-chlorophenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine and 20 ml of dimethylformamide was added 0.6 g of sodium hydride and the mixture was stirred for 15 minutes. To this was further added 3.4 g of fluoromethylsulfate, and stirring was continued for 1.5 hours at room temperature. After the reaction was finished, the solvent was distilled off from the resulting mixture under reduced pressure. The residue thus obtained was diluted with water, extracted with ether and dehydrated. The ether solution was applied on a column of alumina, and then eluted with ether. The ether was evaporated from the eluate, and the residue was recrystallized from a mixture of ether and petroleum ether to give 2.1 g of 1-(m-chlorophenyl)-3-methyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 139° - 140° C.

Workup

  1. stirringstirring
  2. waitwas continued for 1.5 hours at room temperature
  3. distillationthe solvent was distilled off from the resulting mixture under reduced pressure
  4. customThe residue thus obtained
  5. extractionextracted with ether
  6. washeluted with ether
  7. customThe ether was evaporated from the eluate, and the residue
  8. customwas recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-be2a340c10dc4a89bcfe1d115e638aab
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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