Acetic Anhydride → 6-Amino-1-benzyluracil

HRID 2114601Notes

Reaction equation

HRID 2114601 reaction equation
[CH2:1]([NH:8][C:9]([NH2:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:12]([CH2:14][C:15](O)=[O:16])#[N:13].CC(OC(C)=O)=O>CCOCC>[CH2:1]([N:8]1[C:12]([NH2:13])=[CH:14][C:15](=[O:16])[NH:11][C:9]1=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 9740Cyanoacetic acidHCID 10853Benzylurea

Product 1

HCID 2507466-Amino-1-benzyluracilYield 70%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
77.5 °C

Procedure

A mixture of benzylurea (33.3 mmol), 2-cyanoacetic acid (36.63 mmol) and Ac2O (20 mL) was heated at 75-80° C. for 2 hours. After cooling to room temperature, 30 mL of Et2O was added and the resultant suspension was stirred for 1 h. The solid intermediate was filtered, suspended in a mixture of water (30 mL) and ethanol (15 mL) and heated at 80-85° C. 5 mL of 10% NaOH were slowly added. After 30 minutes, the reaction mixture was concentrated, acidified with 10% HCl and the precipitate collected by filtration (Yellow solid. Yield 70-80%).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationThe solid intermediate was filtered
  3. additionsuspended in a mixture of water (30 mL) and ethanol (15 mL)
  4. temperatureheated at 80-85° C
  5. addition5 mL of 10% NaOH were slowly added
  6. concentrationthe reaction mixture was concentrated
  7. filtrationthe precipitate collected by filtration (Yellow solid. Yield 70-80%)

Sources & evidence

ORD record
ord-3741d0e0b2d5412c88a38cbd56e3694e
Source dataset
uspto-grants-2008_10
Patent number
US07435740B2

Reaction notes

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