Tetrahydrofuran → 1-(3-Iodophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

HRID 436406Notes

Reaction equation

HRID 436406 reaction equation
[I:1][C:2]1[CH:3]=[C:4]([CH:14]=[CH:15][CH:16]=1)[NH:5][C:6]1[C:11]([CH2:12][NH2:13])=[CH:10][CH:9]=[CH:8][N:7]=1.[O:17]1CCC[CH2:18]1>CC(C)=O>[I:1][C:2]1[CH:3]=[C:4]([N:5]2[C:6]3[N:7]=[CH:8][CH:9]=[CH:10][C:11]=3[CH2:12][NH:13][C:18]2=[O:17])[CH:14]=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 21452453HCID 21452453, compound

Product 1

HCID 132593321-(3-Iodophenyl)-3,4-dihydropyrido[2,3-d]pyrimidin-2(1H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 3.3 g of 2-(m-iodoanilino)-3-aminomethylpyridine and 30 ml of dry tetrahydrofuran was added 3.2 g of N,N'-carbonyldiimidazole and the mixture was heated under reflux for 12 hours. After the reaction was complete, the solvent was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was dissolved in acetone. The acetone solution was placed on a column of alumina and eluted with acetone. The eluate was concentrated and left to yield 2.5 g of 1-(m-iodophenyl)-2-oxo-1,2,3,4-tetrahydropyrido[2,3-d]pyrimidine as colorless needles, melting at 175° - 177° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 12 hours
  3. customthe solvent was removed from the reaction mixture by distillation under reduced pressure
  4. customThe residue thus obtained
  5. washeluted with acetone
  6. concentrationThe eluate was concentrated
  7. waitleft

Sources & evidence

ORD record
ord-b160a19d7d28440c84a267054daef3b3
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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