Ethyl formate → HCID 178516450, compound

HRID 1051754Notes

Reaction equation

HRID 1051754 reaction equation
C([O:4][CH2:5][CH3:6])(=O)C.[CH:7](OCC)=O.[O-]CC.[Na+].[NH:16]1[C:20]([NH2:21])=[CH:19][CH:18]=[N:17]1>C1(C)C=CC=CC=1>[N:17]1[N:16]2[C:5]([OH:4])=[CH:6][CH:7]=[N:21][C:20]2=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 8025Ethyl formateHCID 8857Ethyl AcetateHCID 74561Pyrazol-3-ylamineHCID 2723922Sodium ethoxide

Product 1

HCID 178516450HCID 178516450, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a mixture of ethyl acetate (88 g, 1.0 mol, 1.0 eq) and ethyl formate (74 g, 1.0 mol, 1.0 eq) in toluene (100 mL), sodium ethoxide (68 g, 1.0 mol, 1.0 eq) is added and the resulting mixture is stirred at RT overnight. The reaction mixture is concentrated in vacuo to remove the solvent. The resulting residue is suspended in EtOH (100 mL) and then 1H-pyrazol-5-amine (41.5 g, 0.5 mol, 0.5 eq) is added in portions to the mixture. The resulting mixture is stirred at reflux for 5 h and concentrated in vacuo. The residue is suspended in ice-water (200 mL) and neutralized with conc. HCl to adjust pH to 1. The resulting solid is collected by filtration and dried in vacuo to afford the product, pyrazolo[1,5-a]pyrimidin-7-ol (C-1).

Workup

  1. additionis added
  2. concentrationThe reaction mixture is concentrated in vacuo
  3. customto remove the solvent
  4. stirringThe resulting mixture is stirred
  5. temperatureat reflux for 5 h
  6. concentrationconcentrated in vacuo
  7. filtrationThe resulting solid is collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-57bf639a649743588d04ac7990fa28e0
Source dataset
uspto-grants-2016_07
Patent number
US09388183B2

Reaction notes

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