Ethyl Acetoacetate → 3-Allyl-6-methyluracil

HRID 985463

Reaction equation

HRID 985463 reaction equation
[CH2:1]([NH:4][C:5]([NH2:7])=[O:6])[CH:2]=[CH2:3].[C:8](OCC)(=[O:13])[CH2:9][C:10]([CH3:12])=O.[OH-].[K+]>C(O)C.Cl.CO>[CH2:1]([N:4]1[C:8](=[O:13])[CH:9]=[C:10]([CH3:12])[NH:7][C:5]1=[O:6])[CH:2]=[CH2:3]

Participants

7

Reactant 3

HCID 8868Ethyl AcetoacetateHCID 11181AllylureaHCID 14797Potassium Hydroxide

Product 1

HCID 136020473-Allyl-6-methyluracil

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To allylurea (25 g, 25 mol) in ethanol (10 mL) was added ethyl acetoacetate (31.86 mL, 25 mol) and 10 drops conc. HCl. After 12 days at room temperature, concentration gave an oil which was dissolved in MeOH. KOH (22.5 g, 0.34 mol) was added and the solution refluxed for 1 hour. After neutralization, the resulting solid 1 was collected. Yield 2.7 g (7%). NMR (CDCl3) δ: 2.16 (3H, s), 4.52 (2H, d), 5.18 (1H, d), 5.23 (1H, d), 5.60 (1H, s), 5.82-5.93 (1H, m), 10.3 (1H, s).

Workup

  1. concentrationconcentration
  2. customgave an oil which
  3. temperaturethe solution refluxed for 1 hour
  4. customAfter neutralization, the resulting solid 1 was collected

Sources & evidence

ORD record
ord-37a753e57f2a4877acb3d87e58643f7f
Source dataset
uspto-grants-2005_03
Patent number
US06872728B2

Linked notes

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