Adenine → HCID 13536441, compound

HRID 2413514Notes

Reaction equation

HRID 2413514 reaction equation
[S:1]1[CH:5]=[CH:4][C:3]([C:6](Cl)=[O:7])=[CH:2]1.[N:9]1[C:17]([NH2:18])=[C:16]2[C:12]([N:13]=[CH:14][NH:15]2)=[N:11][CH:10]=1>N1C=CC=CC=1>[CH:2]1[S:1][CH:5]=[CH:4][C:3]=1[C:6]([NH:18][C:17]1[N:9]=[CH:10][N:11]=[C:12]2[C:16]=1[NH:15][CH:14]=[N:13]2)=[O:7]

Participants

4

Reactant 2

HCID 190AdenineHCID 27763773-Thenoyl chloride

Product 1

HCID 13536441HCID 13536441, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

62.6 g (0.439 mole) of thiophene-3-carbonyl chloride are added to a suspension of 19.7 g (0.146 mole) of adenine in 100 ml of dry pyridine. The mixture is refluxed for 10 hours, the pyridine is distilled off, the residue is taken up in chloroform, the solution is washed with dilute sodium bicarbonate solution and dried over sodium sulfate, and the solvent is then stripped off in a rotary evaporator. The solid residue is stirred repeatedly with cyclohexane and then recrystallized from ethanol and dried at about 40° C. under reduced pressure. 6-(3-Thenoylamino)-purine is obtained in a yield of 60%.

Workup

  1. temperatureThe mixture is refluxed for 10 hours
  2. distillationthe pyridine is distilled off
  3. washthe solution is washed with dilute sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is then stripped off in a rotary evaporator
  6. customrecrystallized from ethanol
  7. customdried at about 40° C. under reduced pressure

Sources & evidence

ORD record
ord-aec47a022e1740a7b713de7f63dd8bc5
Source dataset
uspto-grants-1988_01
Patent number
US04718936

Reaction notes

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