Ethyl cyanoacetate → 6-Amino-1-propyluracil

HRID 411992Notes

Reaction equation

[CH2:1]([NH:4][C:5]([NH2:7])=[O:6])[CH2:2][CH3:3].[C:8](CC(OCC)=O)#[N:9].[O-:16][CH2:17][CH3:18].[Na+]>>[NH2:9][C:8]1[N:4]([CH2:1][CH2:2][CH3:3])[C:5](=[O:6])[NH:7][C:17](=[O:16])[CH:18]=1

Participants

Reactant 3

HCID 7764Ethyl cyanoacetate

HCID 12303Propylurea

HCID 2723922Sodium ethoxide

Product 1

HCID 1045626-Amino-1-propyluracil

Procedure

This method was utilized to prepare the N-3 propylpurines. The starting material used was n-propyl urea condensed with ethyl cyanoacetate in the presence of sodium ethoxide to yield the 6-amino-1-propylpyrimidinedione in moderate yield. Commercially available 3-n-propylxanthine could also be used as the starting material.

Sources & evidence

ORD record: ord-e753900eb5ad4814b93918e0d23cd31b
Source dataset: uspto-grants-2003_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06562819B2

Reaction notes

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