Sulfuric Acid → HCID 178456487, compound

HRID 395877Notes

Reaction equation

HRID 395877 reaction equation
[N-:1]=[N+]=[N-].[Na+].OS(O)(=O)=O.[O:10]=[C:11]1[CH2:16][CH:15]2[CH:17]([C:18]3[NH:26][C:25]4[C:24](=[O:27])[N:23]([CH2:28][CH2:29][CH3:30])[C:22](=[O:31])[N:21]([CH2:32][CH2:33][CH3:34])[C:20]=4[N:19]=3)[CH:12]1[CH2:13][CH2:14]2.C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl>[O:10]=[C:11]1[NH:1][CH2:16][CH:15]2[CH:17]([C:18]3[NH:19][C:20]4[N:21]([CH2:32][CH2:33][CH3:34])[C:22](=[O:31])[N:23]([CH2:28][CH2:29][CH3:30])[C:24](=[O:27])[C:25]=4[N:26]=3)[CH:12]1[CH2:13][CH2:14]2

Participants

6

Reactant 4

HCID 1118Sulfuric AcidHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 18173116HCID 18173116, compound

Product 1

HCID 178456487HCID 178456487, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a solution of NaN3 (65 mg) in CHCl3 (2 ml) was added H2SO4 (0.5 ml). The resulting solution was cooled to 0° C. 8-(2-Oxo-bicyclo[2.2.1]hept-7-yl)-1,3-dipropyl-3,7-dihydro-purine-2,6-dione (173 mg) in CHCl3 (3 ml) was added. The resulting solution was stirred at room temperature for 3 hrs. The reaction mixture was poured over ice and neutralized with NaHCO3, extracted with ethyl acetate (3×25 ml). The combined extract was dried over MgSO4, filtered, and concentrated. The crude product was purified by recrystallization from MeOH. Yield 155 mg. Mass (ES+ 360).

Workup

  1. extractionextracted with ethyl acetate (3×25 ml)
  2. extractionThe combined extract
  3. dry with materialwas dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product was purified by recrystallization from MeOH

Sources & evidence

ORD record
ord-73599f7224474ab5bf68540cc96b0164
Source dataset
uspto-grants-2003_08
Patent number
US06605600B1

Reaction notes

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