Sodium Hydroxide → N9-benzyl-8-(2-phosphonoethylamino)adenine

HRID 1594606Notes

Reaction equation

HRID 1594606 reaction equation
[CH2:1]([N:8]1[C:16](Br)=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][CH2:20][CH2:21][P:22](=[O:25])([O-:24])[O-:23].[OH-].[Na+]>C(O)C.O>[CH2:1]([N:8]1[C:16]([NH:19][CH2:20][CH2:21][P:22]([OH:25])([OH:24])=[O:23])=[N:15][C:14]2[C:9]1=[N:10][CH:11]=[N:12][C:13]=2[NH2:18])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 99045519-Benzyl-8-bromoadenineHCID 23421211HCID 23421211, compound

Product 1

HCID 42637648N9-benzyl-8-(2-phosphonoethylamino)adenine

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of N9-benzyl-8-bromoadenine (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 N9-benzyl-8-(2-phosphonoethylamino)adenine (3.1). Exact mass calculated for C14H17N6O3P+H+: 349.1178. Found: 349.1180.

Workup

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

Sources & evidence

ORD record
ord-d8b92ad73ba7448398e559909f0780e2
Source dataset
uspto-grants-2001_09
Patent number
US06284748B1

Reaction notes

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