Ammonia → 2-Aminoadenosine

HRID 2212474Notes

Reaction equation

HRID 2212474 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 generation 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 evaportaion, or open and re-seal the Parr bomb under a dry nitrogen atmosphere.

Workup

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

Sources & evidence

ORD record
ord-3ff4d942f8874591acd4a4f4ae544b4b
Source dataset
uspto-grants-2006_09
Patent number
US07101993B1

Reaction notes

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