Sodium Hydroxide → 2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carboxylic acid

HRID 1946078Notes

Reaction equation

HRID 1946078 reaction equation
[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([CH:18]=[O:19])[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2].[OH-:30].[Na+]>C(O)C.[N+]([O-])([O-])=O.[Ag+]>[CH2:1]([C:3]1[N:7]([C:8]2[N:16]=[C:15]3[C:11]([N:12]=[C:13]([C:18]([OH:30])=[O:19])[N:14]3[CH3:17])=[C:10]([N:20]3[CH2:25][CH2:24][O:23][CH2:22][CH2:21]3)[N:9]=2)[C:6]2[CH:26]=[CH:27][CH:28]=[CH:29][C:5]=2[N:4]=1)[CH3:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 596059872-(2-Ethylbenzoimidazol-1-yl)-9-methyl-6-morpholin-4-yl-9H-purine-8-carbaldehyde

Product 1

HCID 596053252-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carboxylic acidYield 97%

Reagents, catalysts & solvents 2

HCID 24470Silver NitrateCatalystHCID 702EthanolSolvent

Procedure

To a suspension of 2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carbaldehyde (15 g, 38 mmol) in ethanol was added silver nitrate (8.1 g, 48 mmol) and a 1.5 M NaOH solution (150 mL). The resulting mixture was stirred at room temperature for 30 minutes prior to filtering through celite. The solution was then concentrated. To the residual solid was added water and made basic by adding 1M NaOH (cloudy mixture). The mixture was then washed with DCM. The aqueous layer was then made acidic (pH 2) by adding concentrated HCl. The acidic mixture was then concentrated under vacuum. A precipitate slowly formed during the concentration. After the volume was reduced by ⅓, the suspension was cooled in an ice-bath for 15 minutes before being filtered to collect the solid. The solid was then dried under vacuum to give 2-(2-ethyl-1H-benzo[d]imidazol-1-yl)-9-methyl-6-morpholino-9H-purine-8-carboxylic acid as a beige powder (15.2 g, 97%). LCMS m/z: 408.3 (MH+)

Workup

  1. filtrationto filtering through celite
  2. concentrationThe solution was then concentrated
  3. additionTo the residual solid was added water
  4. additionby adding 1M NaOH (cloudy mixture)
  5. washThe mixture was then washed with DCM
  6. additionmade acidic (pH 2) by adding concentrated HCl
  7. concentrationThe acidic mixture was then concentrated under vacuum
  8. customA precipitate slowly formed during the concentration
  9. temperaturethe suspension was cooled in an ice-bath for 15 minutes
  10. filtrationbefore being filtered
  11. customto collect the solid
  12. customThe solid was then dried under vacuum

Sources & evidence

ORD record
ord-6c332ba7dc6047c5bcd821b6f26dd924
Source dataset
uspto-grants-2013_03
Patent number
US08394796B2

Reaction notes

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