Benzaldehyde → 2-Amino-4-oxo-6-phenyl-1,4-dihydro-5-pyrimidinecarbonitrile

HRID 1161729Notes

Reaction equation

HRID 1161729 reaction equation
[CH:1](=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)(O)O.[NH2:13][C:14]([NH2:16])=[NH:15].[C:17]([CH2:19][C:20](OCC)=[O:21])#[N:18].C([O-])(=O)C.[Na+]>N1C=CC=CC=1>[NH2:15][C:14]1[NH:16][C:20](=[O:21])[C:19]([C:17]#[N:18])=[C:1]([C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[N:13]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 7764Ethyl cyanoacetateHCID 286947Carbonic acid-guanidine (1:1)HCID 517045Sodium Acetate

Product 1

HCID 1357249972-Amino-4-oxo-6-phenyl-1,4-dihydro-5-pyrimidinecarbonitrile

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Benzaldehyde (15 g, 141.3 mmol, 1 eq), guanidine carbonate (25.47 g, 141.3 mmol, 1 eq), ethyl cyanoacetate (15.99 g, 141.3 mmol, 1 eq) and anhydrous sodium acetate (11.59 g, 141.3 mmol, 1 eq) were added to 300 ml anhydrous pyridine and refluxed for 4 hours. The reaction was then cooled to room temperature and the solvent was removed under reduced pressure. The brown residue was triturated with 400 ml aqueous acetic acid (30%) and filtered off. The yellow solid was then triturated with 300 ml diethyl ether and filtered off to yield 2-amino-6-oxo-4-phenyl-1,6-dihydro-pyrimidine-5-carbonitrile as an off-white solid.

Workup

  1. temperaturerefluxed for 4 hours
  2. customthe solvent was removed under reduced pressure
  3. customThe brown residue was triturated with 400 ml aqueous acetic acid (30%)
  4. filtrationfiltered off
  5. customThe yellow solid was then triturated with 300 ml diethyl ether
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-f0829968df394d458bb9e0412a9d2a07
Source dataset
uspto-grants-2010_10
Patent number
US07820658B2

Reaction notes

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