Triethylamine → 9-(2-Hydroxyethylthiomethyl)adenine

HRID 848093Notes

Reaction equation

HRID 848093 reaction equation
Cl[CH2:2][S:3][CH2:4][CH2:5][O:6]C(=O)C.Cl[C:11]1[N:19]=[CH:18][N:17]=[C:16]2[C:12]=1[NH:13][CH:14]=[N:15]2.C([N:22](CC)CC)C>CN(C)C=O>[OH:6][CH2:5][CH2:4][S:3][CH2:2][N:15]1[CH:14]=[N:13][C:12]2[C:16]1=[N:17][CH:18]=[N:19][C:11]=2[NH2:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53592776-ChloropurineHCID 128996102-Acetoxyethyl chloromethyl sulfide

Product 1

HCID 128995919-(2-Hydroxyethylthiomethyl)adenine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Following the procedure of Schaeffer, et al. J. Med. Chem. 14, 367 (1971), 2-acetoxyethyl chloromethyl sulfide (3.37 g) was added to a mixture of 6-chloropurine (3.09 g), triethylamine (2.23 g) and dimethylformamide (20 ml). The reaction mixture was stirred at room temperature for 90 hours and the solvent then removed under reduced pressure. The residual oil was dissolved in chloroform (30 ml) and placed on a column of Florisil (200 g) in chloroform. Elution with chloroform resulted in the desired product in 2.1 liters of eluate (after discarding the initial 300 ml collected). The solvent was evaporated to give a residual oil. Ether-pet.ether was added and the mixture chilled to give 9-(2-acetoxyethylthiomethyl)-6-chloropurine (1.4 g, mp 82°-87° C.). Recrystallization from ether gave white prisms m.p. 89°-91° C.

Workup

  1. customthe solvent then removed under reduced pressure
  2. dissolutionThe residual oil was dissolved in chloroform (30 ml)
  3. washElution with chloroform

Sources & evidence

ORD record
ord-a0d2b050f58043e7bee8f49fee938939
Source dataset
uspto-grants-1981_10
Patent number
US04294831

Reaction notes

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