Ammonia → ara-DAP

HRID 1076171Notes

Reaction equation

HRID 1076171 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:31][C@H:30]([CH2:32][O:33]CC3C=CC=CC=3)[C@@H:21]([O:22]CC3C=CC=CC=3)[C@@H:12]2[O:13]CC2C=CC=CC=2)=[C:4]([NH2:41])[N:3]=1.N.[Na].[Cl-].[NH4+]>>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@@H:11]2[O:31][C@H:30]([CH2:32][OH:33])[C@@H:21]([OH:22])[C@@H:12]2[OH:13])=[C:4]([NH2:41])[N:3]=1

Participants

5

Reactant 4

HCID 222AmmoniaHCID 25517Ammonium ChlorideHCID 5360545Sodium2×HCID 108969412-Amino-9-(2,3,5-tri-O-benzyl-beta-D-arabinofuranosyl)adenine

Product 1

HCID 73662ara-DAP

Procedure

To 1 g. of the product of example II was added 200 ml. of liquid ammonia. Small pieces of sodium were added until the blue color persisted for several minutes. A total of 350 mg. of sodium was used. The blue color was discharged with a few crystals of ammonium chloride. The ammonia was evaporated under a stream of nitrogen and the residue was triturated with 50 ml. of benzene. The insoluble residue was taken up in a few ml. of water and neutralized with acetic acid. The product (500 mg.), after recrystallization from water, melted at 257°-259° with decomposition. The 2,6-diamino-9-(β-D-arabinofuranosyl)purine showed a λ max = 253,290 mμ at pH 1, and λ max = 257,279 mμ at pH 11.

Workup

  1. waitpersisted for several minutes
  2. customThe ammonia was evaporated under a stream of nitrogen
  3. customthe residue was triturated with 50 ml
  4. customThe product (500 mg.), after recrystallization from water, melted at 257°-259° with decomposition

Sources & evidence

ORD record
ord-c3f5fc4b88864d09a38077777f9a51f9
Source dataset
uspto-grants-1976_05
Patent number
US03956277

Reaction notes

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