Ammonia → 5-Bromo-2'-deoxyuridine

HRID 1587278

반응식

HRID 1587278 반응식
[N:1]([CH:4]([OH:20])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([Br:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19])=[N+]=[N-].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N>N1C=CC=CC=1>[Br:18][C:16]1[C:14](=[O:15])[NH:13][C:11](=[O:12])[N:10]([CH:17]=1)[C@@H:8]1[O:9][C@H:5]([CH2:4][OH:20])[C@@H:6]([OH:19])[CH2:7]1.[NH2:1][CH:4]([OH:20])[C@H:5]1[O:9][C@@H:8]([N:10]2[CH:17]=[C:16]([Br:18])[C:14](=[O:15])[NH:13][C:11]2=[O:12])[CH2:7][C@@H:6]1[OH:19]

참가 물질

6

반응물 3

HCID 222AmmoniaHCID 11776TriphenylphosphineHCID 544499215'-Azido-5-bromo-2'-deoxyuridine

생성물 2

HCID 60355-Bromo-2'-deoxyuridineHCID 538627455'-Amino-5-bromo-2'-deoxyuridine

시약·촉매·용매 1

HCID 1049Pyridine용매

실험 절차

The 5'-azido derivative of 5-bromo-2'-deoxy uridine is prepared via the method described above. The 5'-azido-5-bromo-2'-deoxyuridine (1 mmol) is treated with triphenyl phosphine (1.5 mmol) in pyridine at room temperature for 2 h. Concentrated ammonia (1 ml) is added to the reaction vessel. After 14 h the solvent is removed under vacuum. The residue is dissolved in THF and this solution is added to hexanes. The precipitate is collected and the solid triturated with the appropriate solvent to afford the 5'-amino-5-bromo-2'-deoxyuridine.

후처리

  1. customAfter 14 h the solvent is removed under vacuum
  2. dissolutionThe residue is dissolved in THF
  3. additionthis solution is added to hexanes
  4. customThe precipitate is collected
  5. customthe solid triturated with the appropriate solvent

출처 및 근거

ORD 기록
ord-d829be7038bf463ca5d588ce10665c9e
출처 데이터셋
uspto-grants-1993_06
특허 번호
US05217866

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