Ammonium Hydroxide → 2-Chloroadenosine

HRID 248131

Reaction equation

HRID 248131 reaction equation
C([C@@:4]1([OH:29])[C@:8](C(=O)C)([OH:9])[C@@H:7]([CH2:13][O:14]C(=O)C)[O:6][C@H:5]1[N:18]1[CH:26]=[N:25][C:24]2[C:19]1=[N:20][C:21]([Cl:28])=[N:22][C:23]=2Cl)(=O)C.[OH-].[NH4+:31]>O1CCCC1>[Cl:28][C:21]1[N:22]=[C:23]([NH2:31])[C:24]2[N:25]=[CH:26][N:18]([C:19]=2[N:20]=1)[C@@H:5]1[O:6][C@H:7]([CH2:13][OH:14])[C@@H:8]([OH:9])[C@H:4]1[OH:29]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 1317178999-(2',3',5'-O-triacetyl-b-D-ribofuranosyl)-2,6-dichloropurine

Product 1

HCID 89742-Chloroadenosine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound of Example 3 (271 g, 606 M), concentrated ammonium hydroxide (4 L) and tetrahydrofuran (0.5 L) is stirred at room temperature under nitrogen for 4 days. The solvent volume is reduced in vacuo and the resulting residue is triturated with absolute ethanol. The title compound is precipitated out of the ethanolic solvent to yield a light brown solid, (159 g, 87%).

Workup

  1. customthe resulting residue is triturated with absolute ethanol
  2. customThe title compound is precipitated out of the ethanolic solvent
  3. customto yield a light brown solid, (159 g, 87%)

Sources & evidence

ORD record
ord-48f537549a924049abcf925e59802984
Source dataset
uspto-grants-1993_05
Patent number
US05208327

Linked notes

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