Sodium Bicarbonate → 4-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-one

HRID 1787791Notes

Reaction equation

HRID 1787791 reaction equation
[N:1]([O-])=O.[Na+].[CH2:5]([N:10]1[C:18]2[N:17]=[CH:16][NH:15][C:14]=2[C:13](=[O:19])[NH:12]/[C:11]/1=[N:20]\[NH2:21])[CH2:6][CH2:7][CH2:8][CH3:9].C([O-])(O)=O.[Na+]>Cl>[CH2:5]([N:10]1[C:18]2[N:17]=[CH:16][NH:15][C:14]=2[C:13](=[O:19])[N:12]2[N:1]=[N:21][N:20]=[C:11]12)[CH2:6][CH2:7][CH2:8][CH3:9]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 23668193Sodium NitriteHCID 178446164HCID 178446164, compound

Product 1

HCID 576002974-pentyl-4,7-dihydro-8H-tetrazolo[1,5-a]purin-8-oneYield 60.7%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A saturated aqueous NaNO2 (130 mg, 1.89 mmol) solution was added dropwise to a solution of (2E)-3-pentyl-3,7-dihydro-1H-purine-2,6-dione 2-hydrazone (150 mg, 0.63 mmol) in 5% aqueous HCl solution (3 ml) under stirring at room temperature. The mixture was stirred at room temperature for 1 hour. The mixture was neutralized by saturated NaHCO3 solution and extracted by ethyl acetate (3×). The combined organic phases were washed by brine and dried over MgSO4. The filtration and evaporation of solvent gave the desired product (94.6 mg, 60.7%) as white solid. LCMS calculated for C10H14N7O(M+H): 248.1; found: 248.0.

Workup

  1. stirringThe mixture was stirred at room temperature for 1 hour
  2. extractionextracted by ethyl acetate (3×)
  3. washThe combined organic phases were washed by brine
  4. dry with materialdried over MgSO4
  5. filtrationThe filtration and evaporation of solvent

Sources & evidence

ORD record
ord-38f8855b60e64eb4b4fb666f96d20f37
Source dataset
uspto-grants-2009_03
Patent number
US07511050B2

Reaction notes

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