Diethyl Malonate → HCID 178439635, compound

HRID 1892157Notes

Reaction equation

HRID 1892157 reaction equation
[Na].[CH:2]([C:5]1[CH:6]=[N:7][NH:8][C:9]=1[NH2:10])([CH3:4])[CH3:3].[C:11](OCC)(=[O:18])[CH2:12][C:13](OCC)=[O:14]>CCO>[CH:2]([C:5]1[CH:6]=[N:7][N:8]2[C:13]([OH:14])=[CH:12][C:11]([OH:18])=[N:10][C:9]=12)([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 7761Diethyl MalonateHCID 5360545SodiumHCID 190022014-(Propan-2-yl)-1H-pyrazol-5-amine

Product 1

HCID 178439635HCID 178439635, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium (1.58 g, 68.7 mmol) was dissolved in EtOH (250 mL) and to this solution was added 4-isopropyl-1H-pyrazol-5-amine (7.17 g, 57 mmol) and diethyl malonate (10.2 mL, 63 mmol). The solution was heated under reflux for 16 h, cooled to rt and concentrated in vacuo. The residue was dissolved in water (60 mL) and acidified to pH=3 with 2 M HCl and the formed precipitate collected by filtration. 3-Isopropyl-5,7-dihydroxypyrazolo[1,5-α]pyrimidine was obtained as an off-white solid (8.10 g, 35% over three steps). M.p. 242-243° C. (ethanol).

Workup

  1. temperatureThe solution was heated
  2. temperatureunder reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in water (60 mL)
  5. filtrationthe formed precipitate collected by filtration

Sources & evidence

ORD record
ord-ed023c07e3cb423dbd76a8a57ccf5d85
Source dataset
uspto-grants-2013_08
Patent number
US08507673B2

Reaction notes

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