1,3-Propanedithiol → 2-Fluoroadenine

HRID 1646670Notes

Reaction equation

HRID 1646670 reaction equation
C(N(CC)CC)C.[N:8]([C:11]1[N:19]=[C:18]([F:20])[N:17]=[C:16]2[C:12]=1[NH:13][CH:14]=[N:15]2)=[N+]=[N-].C(S)CCS>CO>[F:20][C:18]1[N:17]=[C:16]2[C:12]([NH:13][CH:14]=[N:15]2)=[C:11]([NH2:8])[N:19]=1

Participants

5

Reactant 3

HCID 80131,3-PropanedithiolHCID 8471TriethylamineHCID 198012676-azido-2-fluoro-7H-purine

Product 1

HCID 127902-FluoroadenineYield 92.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Triethylamine (0.40 mL) was added via syringe to a solution of 6-azido-2-fluoropurine (0.256 g) and 1,3-propanedithiol (0.29 mL) in methanol (13.5 mL). After 15 minutes the reaction was complete as judged by TLC and a white precipitate had formed. The precipitate was collected by filtration and washed with two 10 mL portions of methanol and then dried to obtain 0.203 g of 2-fluoroadenine, mp>300° C. This material was identical to an authentic sample by TLC, NMR and IR.

Workup

  1. customa white precipitate had formed
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with two 10 mL portions of methanol
  4. customdried

Sources & evidence

ORD record
ord-d089e88f144d47ecba88e636713cf25d
Source dataset
uspto-grants-1993_01
Patent number
US05180824

Reaction notes

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