Azido(trimethyl)stannane → Hypoxanthine

HRID 382432Notes

Reaction equation

HRID 382432 reaction equation
C(C1C=CC=CC=1C1C=CC(C[N:14]2[C:18]([C:19]([NH2:21])=[O:20])=[C:17]([NH:22][C:23](=O)CC)[N:16]=[CH:15]2)=CC=1)#N.C[Sn](N=[N+]=[N-])(C)C>C1(C)C=CC=CC=1>[NH:21]1[C:19](=[O:20])[C:18]2[NH:14][CH:15]=[N:16][C:17]=2[N:22]=[CH:23]1

Participants

4

Reactant 2

HCID 5104973Azido(trimethyl)stannaneHCID 18360178HCID 18360178, compound

Product 1

HCID 135398638HypoxanthineYield 83%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2.17 g (5.81 mmol) of the amide thus prepared was suspended in 30 ml of toluene and 5.00 g (24.3 mmol) of trimethyl tin azide was added to the suspension, followed by heating for 23 hours while refluxing. Crystals produced was separated by filtration and dissolved in methanol containing 1N hydrochloric acid. The solution was neutralized with 4 N sodium hydroxide aqueous solution. After evaporating methanol, crystals collected by filtration was purified by suspending them in hot methanol, thereby obtaining 1.93 g of 2-ethyl-7-(4-2-tetrazolylphenyl)benzyl)hypoxanthine (yield 83%).

Workup

  1. temperatureby heating for 23 hours
  2. temperaturewhile refluxing
  3. customCrystals produced
  4. customwas separated by filtration
  5. dissolutiondissolved in methanol containing 1N hydrochloric acid
  6. customAfter evaporating methanol, crystals
  7. filtrationcollected by filtration
  8. customwas purified

Sources & evidence

ORD record
ord-2bc02e0a4b2e4d52a01374bbb12c7810
Source dataset
uspto-grants-2001_10
Patent number
US06310070B1

Reaction notes

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