Methanol → 8-Amino-2'-deoxyguanosine

HRID 366971Notes

Reaction equation

HRID 366971 reaction equation
[NH2:1]N.Br[C:4]1[N:5]([C:14]2[N:15]=[C:16]([NH2:22])[NH:17][C:18](=[O:21])[C:19]=2[N:20]=1)[C@@H:6]1[O:13][C@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[CH2:7]1.CO>O>[NH2:1][C:4]1[N:5]([C:14]2[N:15]=[C:16]([NH2:22])[NH:17][C:18](=[O:21])[C:19]=2[N:20]=1)[C@@H:6]1[O:13][C@H:10]([CH2:11][OH:12])[C@@H:8]([OH:9])[CH2:7]1

Participants

5

Reactant 3

HCID 887MethanolHCID 9321HydrazineHCID 13543712613389-03-2

Product 1

HCID 1355088378-Amino-2'-deoxyguanosine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Hydrazine is added to a suspension of 8-bromodeoxyguanosine in water:methanol (150 mL; 1:2) and the resulting solution is heated at reflux for 24 hours. The resulting precipitate is removed by filtration and the filtrate is evaporated to a solid. After repeated evaporations from ethanol, the product is recrystallized from methanol. The purified 8-azido-2'-deoxyguanosine (1.3 g) is dissolved in a mixture of methanol:water (160 mL, 5:3), Raney nickel (10.0 g) is added, and the mixture is heated at reflux for 18 hours. The catalyst is removed by filtration through celite and after washing with water and methanol the filtrate is evaporated to dryness. The resulting solid is recrystallized from methanol to yield 8-aminodeoxyguanosine.

Workup

  1. temperatureat reflux for 24 hours
  2. customThe resulting precipitate is removed by filtration
  3. customthe filtrate is evaporated to a solid
  4. customthe product is recrystallized from methanol
  5. dissolutionThe purified 8-azido-2'-deoxyguanosine (1.3 g) is dissolved in a mixture of methanol
  6. additionwater (160 mL, 5:3), Raney nickel (10.0 g) is added
  7. temperaturethe mixture is heated
  8. temperatureat reflux for 18 hours
  9. customThe catalyst is removed by filtration through celite
  10. washafter washing with water and methanol the filtrate
  11. customis evaporated to dryness
  12. customThe resulting solid is recrystallized from methanol

Sources & evidence

ORD record
ord-529d7500481843ef87f8cf405cf266cf
Source dataset
uspto-grants-2000_10
Patent number
US06132776

Reaction notes

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