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

HRID 1923260노트

반응식

HRID 1923260 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 24470Silver Nitrate촉매HCID 702Ethanol용매

실험 절차

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+)

후처리

  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

출처 및 근거

ORD 기록
ord-2c87f57667224f45aef5f4734bd59106
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08173650B2

반응 노트

불러오는 중…