Ammonia → 2-Aminoadenosine

HRID 341912

Reaction equation

HRID 341912 reaction equation
[NH3:1].O.[C@@H:3]1([N:12]2[C:22]3[N:21]=[C:19]([NH2:20])[NH:18][C:16](=O)[C:15]=3[N:14]=[CH:13]2)[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]1[OH:5].Cl[Si](C)(C)C>O>[NH2:20][C:19]1[N:21]=[C:22]2[C:15]([N:14]=[CH:13][N:12]2[C@@H:3]2[O:11][C@H:8]([CH2:9][OH:10])[C@@H:6]([OH:7])[C@H:4]2[OH:5])=[C:16]([NH2:1])[N:18]=1

Participants

5

Reactant 3

HCID 222Ammonia2×HCID 6397ChlorotrimethylsilaneHCID 135705230Guanosine Hydrate

Product 1

HCID 722002-Aminoadenosine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

This variation of the procedures of Robins, et al. supra, eliminated the need to utilize liquid ammonia in the reaction mixture since the ammonia molecule is generated in situ from the silazane reagent and the water of hydration of the guanosine hydrate starting material. Further, the use of chlorotrimethylsilane was not necessary nor was it necessary to conduct the reaction under anhydrous conditions, do a preliminary evaporation, or open and re-seal the Parr bomb under a dry nitrogen atmosphere.

Workup

  1. customthe reaction under anhydrous conditions
  2. customa preliminary evaporation
  3. customopen and re-seal the Parr bomb under a dry nitrogen atmosphere

Sources & evidence

ORD record
ord-1cfcf0f15bc14dd4893523458c58b8b5
Source dataset
uspto-grants-1999_01
Patent number
US05856466

Linked notes

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