Ethyl cyanoacetate → 6-Amino-1-propyluracil

HRID 1507616

Reaction equation

HRID 1507616 reaction equation
[O-:1][CH2:2][CH3:3].[Na+].[C:5](CC(OCC)=O)#[N:6].[CH2:13]([NH:16][C:17]([NH2:19])=[O:18])[CH2:14][CH3:15]>C(O)C>[NH2:6][C:5]1[N:16]([CH2:13][CH2:14][CH3:15])[C:17](=[O:18])[NH:19][C:2](=[O:1])[CH:3]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 12303PropylureaHCID 2723922Sodium ethoxide

Product 1

HCID 1045626-Amino-1-propyluracilYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium ethoxide (19.99 g, 293.72 mmol, 2 eq) was dissolved in anhydrous ethanol (210 ml) at 50° C. To the solution was added ethyl 2-cyanoacetate (15.67 ml, 146.86 mmol, 1 eq) then 1-propylurea (15 g, 146.86 mmol, 1 eq), and the mixture was stirred at reflux for 24 hours. The solvent was evaporated under reduced pressure, and the residue was dissolved in water (70 ml). The pH of the solution was adjusted to ˜7 by using concentrated HCl. The light yellow solid formed was collected by filtration, washed with water, and dried under vacuum to afford 23.82 g of the desired product (96% yield): The desired isomer was determined via 2D-NMR; 1H NMR (400 MHz, DMSO-d6) δ 10.3 (1H), 6.79 (2H), 4.52 (1H), 3.68-3.70 (2H), 1.50 (2H), 0.85 (3H); m/z (ES+) 170.18

Workup

  1. temperatureat reflux for 24 hours
  2. customThe solvent was evaporated under reduced pressure
  3. dissolutionthe residue was dissolved in water (70 ml)
  4. customThe light yellow solid formed
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under vacuum

Sources & evidence

ORD record
ord-6455bbbd7eeb4c738ffce38197e6e79f
Source dataset
uspto-grants-2015_12
Patent number
US09221821B2

Linked notes

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