Sodium Hydroxide → HCID 178476931, compound

HRID 2197462Notes

Reaction equation

HRID 2197462 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5](Br)[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:30])([O:27]CC)[O:24][CH2:25][CH3:26])[CH:20]=[CH:21][CH:22]=1.[OH-:32].[Na+]>CO>[NH2:1][C:2]1[N:10]=[C:9]([O:11][CH2:12][CH2:13][O:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[C:5]([OH:32])[N:6]2[CH2:16][C:17]1[CH:18]=[C:19]([P:23](=[O:30])([OH:27])[O:24][CH2:25][CH3:26])[CH:20]=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86617440HCID 86617440, compound

Product 1

HCID 178476931HCID 178476931, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Diethyl 3-((6-amino-8-bromo-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate (100 mg, 0.194 mmol) was dissolved in methanol (5 mL) and 1 N aqueous NaOH solution was added. The reaction mixture was heated at reflux and progress was monitored by HPLC. As soon as all the starting material had been consumed, the reaction mixture was acidified with conc. HCL. After heating at reflux for 1 h, the mixture was evaporated to dryness under vacuum. The product was purified by preparative reverse phase HPLC, yielding ethyl hydrogen 3-((6-amino-8-hydroxy-2-(2-methoxyethoxy)-9H-purin-9-yl)methyl)phenylphosphonate Example (K) (18 mg, 22%) as a white powder. 1H-NMR (DMSO) δ: 10.0 (s, 1H), 7.65-7.42 (m, 5H), 6.51 (br, 2H), 4.90 (s, 2H), 4.25 (t, J=4.5 Hz, 2H), 3.84 (quint, J=7 Hz, 2H), 3.57 (t, J=4.5 Hz, 2H), 3.26 (s, 3H), 1.13 (t, J=7 Hz, 3H). 31P-NMR (DMSO) δ: 13.04. MS: 424 (MH+).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux
  3. customAs soon as all the starting material had been consumed
  4. temperatureAfter heating
  5. temperatureat reflux for 1 h
  6. customthe mixture was evaporated to dryness under vacuum
  7. customThe product was purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-d4e32a5b018f430e8929ada0d0f1e5db
Source dataset
uspto-grants-2012_12
Patent number
US08338593B2

Reaction notes

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