Ethyl 3-oxo-4-phenylbutanoate → 2,6-dibenzyl-1H-pyrimidin-4-one

HRID 1729236

Reaction equation

HRID 1729236 reaction equation
[Na].Cl.[C:3]1([CH2:9][C:10]([NH2:12])=[NH:11])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:13]1([CH2:19][C:20](=O)[CH2:21][C:22](OCC)=[O:23])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C(O)C>[C:3]1([CH2:9][C:10]2[N:12]=[C:20]([CH2:19][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:21]=[C:22]([OH:23])[N:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 225855Ethyl 3-oxo-4-phenylbutanoateHCID 5360545SodiumHCID 124155142-Phenylethanimidamide hydrochloride

Product 1

HCID 1785158572,6-dibenzyl-1H-pyrimidin-4-oneYield 34.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of sodium (1.84 g, 80 mmol) in ethanol (200 ml) was added phenylacetamidine hydrochloride (16.2 g, 95.0 mmol) and ethyl 4-phenylacetoacetate (15 g, 72.9 mmol). The mixture was heated under reflux with stirring for 5 days followed by cooling and evaporation in vacuo. Water (150 ml) was added to the residue causing a solid to precipitate which was filtered off and washed thoroughly with water and diethyl ether. Recrystallisation of the solid from a chloroform/hexane mixture afforded 6.9 g 2,4-di(phenylmethyl)-6-hydroxypyrimidine as a white solid. m.pt., 158°-160° C., M+ found: 276.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux
  3. temperatureby cooling
  4. customevaporation in vacuo
  5. additionWater (150 ml) was added to the residue
  6. customto precipitate which
  7. filtrationwas filtered off
  8. washwashed thoroughly with water and diethyl ether
  9. customRecrystallisation of the solid from a chloroform/hexane mixture

Sources & evidence

ORD record
ord-82d63ebf3c5048e2a9da1de12a330986
Source dataset
uspto-grants-1994_07
Patent number
US05332745

Linked notes

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