Sodium Nitrite → 7-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dione

HRID 2200631Notes

Reaction equation

HRID 2200631 reaction equation
[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](N)=[N:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3].N([O-])=[O:16].[Na+]>C(O)(=O)C.O>[CH2:1]([N:4]1[C:12]2[C:11](=[O:13])[NH:10][C:9](=[O:16])[NH:8][C:7]=2[N:6]=[CH:5]1)[CH:2]=[CH2:3]

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 1354353176H-Purin-6-one, 2-amino-1,7-dihydro-7-(2-propen-1-yl)-

Product 1

HCID 598537957-(2-propen-1-yl)-3,7-dihydro-1H-purine-2,6-dioneYield 74.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

To a solution of 7-allyl-2-amino-1H-purin-6(7H)-one (20 g, 104.7 mmol) in acetic acid (500 mL) and water (70 mL) was added a solution of sodium nitrite (30 g, 434.8 mmol) in water (70 mL) dropwise at 50° C. The reaction was stirred at 50° C. for 1 h. The reaction was concentrated and poured into ice-water. The solids that formed were filtered and the filter cake was washed with water and ethanol, then dried under vacuum to give 7-allyl-1H-purine-2,6(3H,7H)-dione (15 g, 74.4% yield) as yellow solid. LCMS retention time 0.555 min; LCMS MH+ 193.

Workup

  1. concentrationThe reaction was concentrated
  2. additionpoured into ice-water
  3. customThe solids that formed
  4. filtrationwere filtered
  5. washthe filter cake was washed with water and ethanol
  6. customdried under vacuum

Sources & evidence

ORD record
ord-bae810d27545479fb4f6c12122b29315
Source dataset
uspto-grants-2016_06
Patent number
US09359359B2

Reaction notes

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