Pyridine → Acridine

HRID 36385

반응식

HRID 36385 반응식
[CH:1]1[CH:6]=[C:5]2[C:7](OP(Cl)O[C:4]2=[CH:3][CH:2]=1)=O.[N:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH2:19](Cl)Cl>CC[N+](CC)(CC)CC.[Br-]>[CH:6]1[C:5]2[C:4](=[N:13][C:18]3[C:17]([CH:7]=2)=[CH:16][CH:15]=[CH:14][CH:19]=3)[CH:3]=[CH:2][CH:1]=1

참가 물질

5

반응물 3

HCID 1049PyridineHCID 6344DichloromethaneHCID 2370102-Chloro-4H-1,3,2-benzodioxaphosphorin-4-one

생성물 1

HCID 9215Acridine수율 65%

시약·촉매·용매 1

HCID 6285Tetraethylammonium Bromide촉매

반응 조건

온도
0 °C

실험 절차

To a cold, stirring methylene chloride solution (30 ml; 0° C.) of 2-chloro-4H-1,2,3-benzodioxaphosphorin-4-one (2.4 ml of 1M methylene chloride solution; 2.4 mmol) and pyridine (0.2 g; 2.4 mmol) was added the DMT-protected pseudonucleoside of Example 2, paragraph A (0.55 g; 0.8 mmol). After stirring at 0° C. for 1 hour, the reaction mixture was poured into 1M TEAB aqueous solution (60 ml). The organic solution was separated, dried, concentrated. The residue was purified by flash column chromatography, eluted with 1% Et3N/CH2Cl2, 1% Et3N/1%CH3OH/CH2Cl2. The combined fraction of the product was washed with 1M TEAB aqueous solution, dried over Na2SO4, and concentrated, affording 0.19 g, 65% of the phosphorylated DMT-protected acridine pseudonucleotide.

후처리

  1. additionwas added the DMT-protected pseudonucleoside of Example 2, paragraph A (0.55 g; 0.8 mmol)
  2. customThe organic solution was separated
  3. customdried
  4. concentrationconcentrated
  5. customThe residue was purified by flash column chromatography
  6. washeluted with 1% Et3N/CH2Cl2, 1% Et3N/1%CH3OH/CH2Cl2
  7. washThe combined fraction of the product was washed with 1M TEAB aqueous solution
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated

출처 및 근거

ORD 기록
ord-13abdcc7b4664668a3fd37e4965d21df
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05414077

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