Sodium Hydroxide → 2-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-8-ylamino)ethylphosphonic acid

HRID 1594607Notes

Reaction equation

HRID 1594607 reaction equation
Br[C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6].[NH2:21][CH2:22][CH2:23][P:24](=[O:27])([O-:26])[O-:25].[OH-].[Na+]>C(O)C.O>[P:24]([CH2:23][CH2:22][NH:21][C:2]1[N:3]([C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:20])[C:18]=2[N:19]=1)[C@@H:4]1[O:12][C@H:9]([CH2:10][OH:11])[C@@H:7]([OH:8])[C@H:5]1[OH:6])([OH:27])([OH:26])=[O:25]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 965448-BromoadenosineHCID 23421211HCID 23421211, compound

Product 1

HCID 445917212-(6-amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-9H-purin-8-ylamino)ethylphosphonic acid

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 8-bromoadenosine (1 mmol), aminoethylphosphonate (2 mmol), and sodium hydroxide (2 mmol) in ethanol-water in a sealed tube was warmed at 110° C. under nitrogen. After 24 h the cooled reaction mixture was purified through preparative HPLC to give 8-(2-phosphonoethylamino)-adenosine (4.1). mp 175° C.; Anal. calcd. for C12H19N6O7P+0.5 H2O: C: 36.10; H: 5.05; N: 21.05; P: 7.76. Found: C: 36.08; H: 4.83; N: 20.36; P: 7.86.

Workup

  1. customAfter 24 h the cooled reaction mixture
  2. customwas purified through preparative HPLC

Sources & evidence

ORD record
ord-3102adbd8fa946f190afb47c6d168b27
Source dataset
uspto-grants-2001_09
Patent number
US06284748B1

Reaction notes

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