Dimethylformamide → 2-Thioadenosine

HRID 1729611

Reaction equation

HRID 1729611 reaction equation
C1(O[N:8]=[C:9]([C:11]2[N:12]=[CH:13][N:14]([C@@H:17]3[O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]3[OH:19])[C:15]=2[NH2:16])[NH2:10])CCCCC1.CN(C)C=O.[C:31](=S)=[S:32]>>[CH:13]1[N:14]([C@@H:17]2[O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]2[OH:19])[C:15]2[C:11](=[C:9]([NH2:10])[NH:8][C:31]([N:16]=2)=[S:32])[N:12]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6348Carbon DisulfideHCID 54291096HCID 54291096, compound

Product 1

HCID 64519652-ThioadenosineYield 76%

Procedure

0.45 g of 5-amino-1-β-D-ribofuranosylimidazole-4-carboxamide O-cyclohexyl-oxime was dissolved in 4 ml of an aqueous solution containing 3 ml of N,N-dimethylformamide, and 1 ml of carbon disulfide was added to the solution. The resulting mixture was allowed to react in an autoclave at 125° C for 5 hours under autogenous pressure (about 10 Kg/cm2), and the reaction product was worked up in the same manner as described in Example 1 to obtain 0.305 g of 2-thioadenosine having a melting point of 197° C (with decomposition) in 76% yield.

Workup

  1. additionwas added to the solution
  2. customto react in an autoclave at 125° C for 5 hours under autogenous pressure (about 10 Kg/cm2)

Sources & evidence

ORD record
ord-e41d7a30a3f64cfc888dab9e8e25555e
Source dataset
uspto-grants-1976_11
Patent number
US03989682

Linked notes

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