Sodium Hydroxide → 2,6-Diaminopurine
Reaction equation
S(O)(O)(=O)=O.[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([NH:11][CH:12]=[N:13]2)=[C:9]([NH2:16])[N:8]=1.[OH-].[Na+]>>[NH2:6][C:7]1[N:15]=[C:14]2[C:10]([NH:11][CH:12]=[N:13]2)=[C:9]([NH2:16])[N:8]=1Participants
Procedure
Generally speaking, compounds of this invention are prepared from 2-acetamido-adenosine-5'-carboxylic acid or from the corresponding 2',3'-isopropylidene derivatives. 2-acetamido-adenosine-5'-carboxylic acid is obtained by reacting 2,6-diaminopurine sulfate with sodium hydroxide to obtain 2,6-diaminopurine which is then reacted with acetic anhydride to yield 2,6-diacetamidopurine, which in turn is converted to a mercuri chloride complex. The mercuri chloride complex of 2,6-diacetamidopurine is then reacted with triacetyl D-ribofuranosyl chloride to obtain 2,6diacetamido-9-(triacetyl-β-D-ribofuranosyl) purine, which is then converted to the corresponding 2-acetamido adenosine by treatment with methanol in the presence of ammonia. Preparation of 2-acetamido adenosine from 2,6-diaminopurine sulfate has been described by J. Davoll & B. A. Lowy [J.A.C.S., 73, 1650 (1951)]. The corresponding isopropylidene compound is obtained by reacting 2-acetamido adenosine with acetone. Potassium permanganate oxidation affords the corresponding 5'-carboxylic acid.
Sources & evidence
- ORD record
- ord-f801efbafdb845d2ba7c802c17e6142a
- Source dataset
- uspto-grants-1976_11
- Patent number
- US03992531
Reaction notes
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