Ammonium Hydroxide → HCID 14503124, compound

HRID 1494508Notes

Reaction equation

HRID 1494508 reaction equation
[NH4+:1].[OH-].[NH2:3][C:4]1[N:12]=[C:11]2[C:7](=[N:8][CH:9]=[N:10]2)[C:6](=[S:13])[N:5]=1>[OH-].[K+]>[NH2:3][C:4]1[N:12]=[C:11]2[C:7]([NH:8][CH:9]=[N:10]2)=[C:6]([S:13][NH2:1])[N:5]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 222885302-Imino-2H-purine-6-thiol

Product 1

HCID 14503124HCID 14503124, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 14797Potassium HydroxideSolvent

Procedure

To an ice-cold 5.25% sodium hypochlorite solution (33.8 mL) was added 7N NH4OH (17.8 mL) and stirred for 10 minutes. A solution of 2-aminopurine-6-thione 1, see A. G. Beaman and R. K. Robins, J. Am. Chem. Soc., 83, 4038, (1961), (1.67 g, 22 mmol) in 2N KOH (11 mL) was added and continued stirring for 25 min at 0.C. The mixture was allowed to stand at 0° C. without stirring for 1.5 h. The precipitate was collected by filtration and washed with small amount of water and EtOH to obtain 1.45 g (36%) of the title compound, mp>250° C.: UV: λmax (pH 1) 325 nm (ε 6,400), 240 nm (sh): λmax (pH 7) 310 nm (ε 5,900), 237 nm (ε 6,800): λmax (pH 11) 312 nm (ε 5,900): 1H NMR (DMSO-d6): δ 5.78 (br s, 2, NH2, exchangeable in D2O), 7.73 (s, 1, C8H): Anal. Calcd for C5H6N6S.1/2 H2O (191.1): C, 31.41: H, 3.27: N, 43.98: S, 16.79. Found: C, 1.89: H, 3.27: N, 43.38: S, 17.19.

Workup

  1. customto stand at 0° C.
  2. stirringwithout stirring for 1.5 h
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with small amount of water and EtOH

Sources & evidence

ORD record
ord-a8fa1ef326f2421293b0f785df339c1c
Source dataset
uspto-grants-1991_06
Patent number
US05026836

Reaction notes

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