6-Methylmercaptopurine → 6-Methylmercaptopurine Riboside

HRID 2256195Notes

Reaction equation

HRID 2256195 reaction equation
[CH3:1][S:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.C([O:15][C@@H:16]1[C@H:20]([O:21]C(=O)C)[C@@H:19]([CH2:25][O:26]C(=O)C)[O:18][CH:17]1Cl)(=O)C>>[CH3:1][S:2][C:3]1[C:4]2[N:5]=[CH:6][N:7]([C@@H:17]3[O:18][C@H:19]([CH2:25][OH:26])[C@@H:20]([OH:21])[C@H:16]3[OH:15])[C:8]=2[N:9]=[CH:10][N:11]=1.[C@@H:17]1([N:7]2[C:8]3[N:9]=[CH:10][N:11]=[C:3]([SH:2])[C:4]=3[N:5]=[CH:6]2)[O:18][C@H:19]([CH2:25][OH:26])[C@@H:20]([OH:21])[C@H:16]1[OH:15]

Participants

4

Reactant 2

HCID 57786-MethylmercaptopurineHCID 133847342,3,5-tri-O-acetyl-D-ribofuranosyl chloride

Product 2

HCID 95706-Methylmercaptopurine RibosideHCID 178521071(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-sulfanylpurin-9-yl)oxolane-3,4-diol

Procedure

6-Methylmercaptopurine riboside is synthesized by condensing 6-methylmercaptopurine with 2,3,5-tri-O-acetyl-D-ribo-furanosyl chloride using the catalyst mercuric chloride followed by deacetylation. Alternatively, 6-methylmercaptopurine riboside can be produced directly by methylation of 6-thioinosine (Fox, J. J. et al., J. Am. Chem. Soc. 80: 1669, 1958).

Sources & evidence

ORD record
ord-b1a83fa837e6425c88af4e5d567513b4
Source dataset
uspto-grants-1997_08
Patent number
US05654286

Reaction notes

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