Diethyl allylmalonate → HCID 178439764, compound

HRID 1452614Notes

Reaction equation

HRID 1452614 reaction equation
[O-]CC.[Na+].[NH2:5][C:6]1[CH:10]=[CH:9][NH:8][N:7]=1.[CH2:11]([CH:14]([C:20](OCC)=[O:21])[C:15](OCC)=[O:16])[CH:12]=[CH2:13]>>[CH2:11]([C:14]1[C:20]([OH:21])=[N:5][C:6]2[N:7]([N:8]=[CH:9][CH:10]=2)[C:15]=1[OH:16])[CH:12]=[CH2:13]

Participants

4

Reactant 3

HCID 74900Diethyl allylmalonateHCID 2723922Sodium ethoxideHCID 178418806HCID 178418806, compound

Product 1

HCID 178439764HCID 178439764, compoundYield 8.1%

Procedure

To an ethanolic solution (0.2 L) containing sodium ethoxide (7.8 g, 0.11 mol), 3-aminopyrazole (5.0 g, 0.6 mol) and diethyl allylmalonate (12 mL, 0.61 mol) were added at room temperature. The resultant mixture was heated under reflux for 24 hr. After the mixture was cooled down to room temperature, the solvent was distilled off. The residue was dissolved in water (150 mL) and the aqueous solution was washed with ethyl acetate. This aqueous layer was acidified by adding 6 mol/L hydrochloric acid, and the resultant precipitate was collected by filtration and dried under reduced pressure to obtain 6-allyl-5,7-dihydroxypyrazolo[1,5-a]pyrimidine (9.3 g).

Workup

  1. additionwere added at room temperature
  2. temperatureunder reflux for 24 hr
  3. distillationthe solvent was distilled off
  4. dissolutionThe residue was dissolved in water (150 mL)
  5. washthe aqueous solution was washed with ethyl acetate
  6. additionby adding 6 mol/L hydrochloric acid
  7. filtrationthe resultant precipitate was collected by filtration
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-04e8631e954e49809a3e90198a49a0a1
Source dataset
uspto-grants-2009_01
Patent number
US07473694B2

Reaction notes

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