Pyridine → HCID 70146783, 화합물

HRID 611462

반응식

HRID 611462 반응식
[OH2:1].[C@@H:2]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[CH2:3]1.N1C=CC=CC=1.[H-].[Na+].[N+:28]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33]Br)([O-:30])=[O:29]>CN(C=O)C>[N+:28]([C:31]1[CH:38]=[CH:37][CH:36]=[CH:35][C:32]=1[CH2:33][C@@:2]1([N:10]2[C:19]3[N:18]=[CH:17][N:16]=[C:14]([NH2:15])[C:13]=3[N:12]=[CH:11]2)[O:9][C@H:6]([CH2:7][OH:8])[C@@H:4]([OH:5])[C@H:3]1[OH:1])([O-:30])=[O:29]

참가 물질

6

반응물 4

HCID 1049PyridineHCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 95491722'-Deoxyadenosine monohydrate

생성물 1

HCID 70146783HCID 70146783, 화합물수율 39.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

2'-Deoxyadenosine monohydrate (538 mg, 2.0 mmol, Aldrich Chemical, Milwaukee, Wisc.) was dried by evaporation with anhydrous pyridine (2 times, 10 ml) under vacuum. The residue was dissolved in anhydrous DMF (10 ml, Aldrich, Milwaukee, Wisc.) under an argon atmosphere, and sodium hydride (88 mg, 2.2 mmol, 1.1 equiv, 60% dispersion in oil) was added and stirred for 40 mins at room temperature. 2-Nitrobenzyl bromide (710 mg, 3.3 mmol, 1.5 equiv) was added and the solution was stirred for 4 hours at room temperature. The DMF was removed by evaporation under vacuum, and the residue was partitioned between ethyl acetate and water (20 ml each). The aqueous phase was extracted with ethyl acetate (20 ml) and the combined extracts were washed with water (20 ml) and dried over magnesium sulfate, filtered and evaporated. The crude product was purified by column chromatography on silica gel (50 g, using 3% MeOH in CH2Cl2) to yield 2'-deoxy-N6 -bis-ortho-nitrobenzyladenosine (320 mg, 30%).

후처리

  1. stirringthe solution was stirred for 4 hours at room temperature
  2. customThe DMF was removed by evaporation under vacuum
  3. customthe residue was partitioned between ethyl acetate and water (20 ml each)
  4. extractionThe aqueous phase was extracted with ethyl acetate (20 ml)
  5. washthe combined extracts were washed with water (20 ml)
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by column chromatography on silica gel (50 g, using 3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-3c2e13034cc941bc92ba7f9e3993e05c
출처 데이터셋
uspto-grants-1999_12
특허 번호
US06001611

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