Methanol → 2-Thioadenosine

HRID 1729616Notes

Reaction equation

HRID 1729616 reaction equation
Cl.[NH2:2][C:3]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[CH:6]=[N:5][C:4]=1[C:17](=[N:19]O)[NH2:18].CO.N1C=CC=CC=1.[C:29](=S)=[S:30]>>[CH:6]1[N:7]([C@@H:8]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[C@H:9]2[OH:10])[C:3]2[C:4](=[C:17]([NH2:18])[NH:19][C:29]([N:2]=2)=[S:30])[N:5]=1

Participants

5

Reactant 4

HCID 887MethanolHCID 1049PyridineHCID 6348Carbon DisulfideHCID 888367015-amino-1-beta-D-ribofuranosylimidazole-4-carboxamide oxime hydrochloride

Product 1

HCID 64519652-ThioadenosineYield 88%

Procedure

To 10.0 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide oxime hydrochloride were added 120 ml of methanol and 120 ml of pyridine to form a solution. 60 ml of carbon disulfide was added to the solution, and the resulting mixture was allowed to react in an autoclave at 120° C for 3 hours under autogenous pressure (about 10 kg/cm2). The reaction mixture was concentrated to dryness, and the residue was dissolved in 1N aqueous ammonia. 100 ml of n-butanol and 50 ml of glacial acetic acid were then added to the solution followed by cooling to crystallize the product to obtain 9.01 g of 2-thioadenosine having a melting point of 199° C (with decomposition) in an 88% yield.

Workup

  1. customto form a solution
  2. customto react in an autoclave at 120° C for 3 hours under autogenous pressure (about 10 kg/cm2)
  3. concentrationThe reaction mixture was concentrated to dryness
  4. dissolutionthe residue was dissolved in 1N aqueous ammonia
  5. addition100 ml of n-butanol and 50 ml of glacial acetic acid were then added to the solution
  6. temperatureby cooling
  7. customto crystallize the product

Sources & evidence

ORD record
ord-e8edbe41fe764ef49b3237af6829ef1c
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Reaction notes

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