Ethyl Acetoacetate → HCID 12229214, compound

HRID 262520Notes

Reaction equation

HRID 262520 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]=O)[CH:2]=1.[C:9]([O:15][CH2:16][CH3:17])(=[O:14])[CH2:10][C:11]([CH3:13])=[O:12]>[Pd].CCOCC>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH:10]([C:11]([CH3:13])=[O:12])[C:9]([O:15][CH2:16][CH3:17])=[O:14])[CH:2]=1

Participants

5

Reactant 2

HCID 8868Ethyl AcetoacetateHCID 103713-Pyridinecarboxaldehyde

Product 1

HCID 12229214HCID 12229214, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

A mixture of pyridine-3-carboxaldehyde (48 g), ethyl acetoacetate (52 g) aqueous piperidine acetate (40% 4.8 g) and 5% palladium on charcoal catalyst (50% wet, 2.48 g) was hydrogenated at 100 p.s.i. at 30° for 22 hours. The mixture was diluted with ether, filtered and the filtrate was evaporated and distilled under reduced pressure to give ethyl α-(3-pyridylmethyl)acetoacetate (b.p. 146°/1 mmHg). This ester was refluxed with thiourea and sodium ethoxide in ethanol, and the mixture was subsequently acidified to give 5-(3-pyridylmethyl)-6-methyl-2-thiouracil m.p. 328°-331°.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated
  3. distillationdistilled under reduced pressure

Sources & evidence

ORD record
ord-589f29bbd71d475f925868298b2f6954
Source dataset
uspto-grants-1979_05
Patent number
US04154834

Reaction notes

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