Dimethylformamide → HCID 13259282, compound

HRID 436415Notes

Reaction equation

HRID 436415 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][NH:11][C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1.CN(C)C=O.[CH2:27](OC(OCC)N(C)C)[CH3:28]>O>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([N:9]2[C:14]3[N:15]=[CH:16][CH:17]=[CH:18][C:13]=3[CH2:12][N:11]([CH2:27][CH3:28])[C:10]2=[O:19])[CH:6]=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70913Dimethylformamide diethylacetalHCID 13259337HCID 13259337, compound

Product 1

HCID 13259282HCID 13259282, compoundYield 18.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 2.9 g of 1-(m-trifluoromethylphenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine, 25 ml of dimethylformamide and 4.4 g of dimethylformamide diethylacetal was reacted at 145° - 150° C for 5 hours. After the reaction was complete, the solvent was distilled off from the 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 eluate was concentrated by evaporation to leave a residue, which was then recrystallized from a mixture of ether and petroleum ether to give 0.6 g of 1-(m-trifluoromethylphenyl)-3-ethyl-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless prisms, melting at 155° - 157° C.

Workup

  1. customwas reacted at 145° - 150° C for 5 hours
  2. distillationthe solvent was distilled off from the mixture under reduced pressure
  3. customThe residue thus obtained
  4. extractionextracted with ether
  5. washeluted with ether
  6. concentrationThe eluate was concentrated by evaporation
  7. customto leave a residue, which
  8. customwas then recrystallized from a mixture of ether and petroleum ether

Sources & evidence

ORD record
ord-18e15e9d30c8414899955d9c71998141
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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