Adenine → N-(3-Thienylmethyl)-9H-purin-6-amine

HRID 2413513Notes

Reaction equation

HRID 2413513 reaction equation
[N:1]1[C:9]([NH2:10])=[C:8]2[C:4]([N:5]=[CH:6][NH:7]2)=[N:3][CH:2]=1.[S:11]1[CH:15]=[CH:14][C:13]([C:16](Cl)=O)=[CH:12]1.N1C=CC=CC=1>O1CCOCC1>[S:11]1[CH:15]=[CH:14][C:13]([CH2:16][NH:10][C:9]2[N:1]=[CH:2][N:3]=[C:4]3[C:8]=2[NH:7][CH:6]=[N:5]3)=[CH:12]1

Participants

5

Reactant 3

HCID 190AdenineHCID 1049PyridineHCID 27763773-Thenoyl chloride

Product 1

HCID 13536440N-(3-Thienylmethyl)-9H-purin-6-amine

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

In the other version of the process, 1 mole equivalent of adenine is heated in a conventional manner (Phytochemistry 16, (1977) 1865) with from 1 to 10, preferably from 2 to 5, mole equivalents of thiophene-3-carbonyl chloride in the presence of a proton acceptor (e.g. pyridine), possibly in a solvent, such as dioxane, at as high as 200° C., and the mixture is worked up in a conventional manner and if necessary recrystallized, for example as described above.

Sources & evidence

ORD record
ord-d1e2bd802d7149e38e0b052534c4a447
Source dataset
uspto-grants-1988_01
Patent number
US04718936

Reaction notes

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