Diethyl Carbonate → HCID 13259282, compound

HRID 436410Notes

Reaction equation

HRID 436410 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[NH:6][C:7]1[C:12]([CH2:13][NH:14][CH2:15][CH3:16])=[CH:11][CH:10]=[CH:9][N:8]=1.[O-:22][CH2:23]C.[Na+].C(=O)(OCC)OCC>O1CCOCC1>[F:21][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([N:6]2[C:7]3[N:8]=[CH:9][CH:10]=[CH:11][C:12]=3[CH2:13][N:14]([CH2:15][CH3:16])[C:23]2=[O:22])[CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7766Diethyl CarbonateHCID 2723922Sodium ethoxideHCID 21452455HCID 21452455, compound

Product 1

HCID 13259282HCID 13259282, compoundYield 96.5%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 2.0 g of 2-(m-trifluoromethylanilino)-3-ethylaminomethylpyridine, 1.0 g of sodium ethoxide and 30 ml of dioxane was added dropwise 2.4 g of diethyl carbonate, and the mixture was heated under reflux for 5 hours. After the reaction was complete, the dioxane was removed from the reaction mixture by distillation under reduced pressure. The residue thus obtained was recrystallized from ether to yield 2.1 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. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customthe dioxane was removed from the reaction mixture by distillation under reduced pressure
  4. customThe residue thus obtained
  5. customwas recrystallized from ether

Sources & evidence

ORD record
ord-65a1faf466ac452b9d5f6c5f0e80ddb8
Source dataset
uspto-grants-1977_02
Patent number
US04009166

Reaction notes

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