Sodium Sulfide → HCID 86751120, compound

HRID 266910Notes

Reaction equation

HRID 266910 reaction equation
[CH3:1][N:2]1[CH:20]=[N:19][C:18]2[N:7]([C@@H:8]3[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:9]3[O:10][CH3:11])[CH:6]=[N:5][C:4]=2[C:3]1=N.CN1C=NC2N([C@@H]3O[C@H](CO)[C@@H](OC)[C@H]3O)C=NC=2C1=N.[S-2:43].[Na+].[Na+]>CN(C)C=O>[CH3:1][N:2]1[CH:20]=[N:19][C:18]2[N:7]([C@@H:8]3[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:9]3[O:10][CH3:11])[CH:6]=[N:5][C:4]=2[C:3]1=[S:43]

Participants

5

Reactant 3

HCID 14804Sodium SulfideHCID 86751121HCID 86751121, compoundHCID 86751122HCID 86751122, compound

Product 1

HCID 86751120HCID 86751120, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction Scheme 2 discloses the presently preferred method for preparing 1-N-,2'-O-dimethyl-6-thioinosine (Compound 25). In accordance with this method, adenosine (Compound 20) is reacted with methylchloride in a polar aprotic solvent, such as dimethylformamide (DMF) or dimethylacetamide (DMA) in the presence of strong base, such as sodium hydride. The resulting 2'-O-methyl adenosine is reacted, without isolation, with iodomethane to introduce the methyl group to the 1-N-position. After the treatment with iodomethane a crude product is obtained which contains approximately 60% of the desired 1-N-,2'-O-dimethyladenosine intermediate, and also contains some 1-N-,3'-O-dimethyladenosine as well as monomethylated derivatives. The crude product is reacted at a moderately elevated temperature (approximately 45° C.) with anhydrous sodium sulfide in anhydrous dimethylformamide, and the resulting crude product is purified by chromatography to yield the desired 1-N-,2'-O-dimethyl-6-thioinosine (Compound 25). ##STR7##

Workup

  1. customthe resulting crude product is purified by chromatography

Sources & evidence

ORD record
ord-02ed3aab6f8b4467a825aef718339857
Source dataset
uspto-grants-1997_07
Patent number
US05652359

Reaction notes

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