Lithium azide → 4-amino-1-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxy-tetrahydrofuran-2-yl]-5-iodo-pyrimidin-2-one

HRID 838928노트

반응식

HRID 838928 반응식
[I:1][C:2]1[C:3]([NH2:27])=[N:4][C:5](=[O:26])[N:6]([CH:25]=1)[C@@H:7]1[O:24][C@H:11]([CH2:12]OS(C2C=CC(C)=CC=2)(=O)=O)[C@@H:9]([OH:10])[CH2:8]1.[N-:28]=[N+:29]=[N-:30].[Li+]>CN(C=O)C>[I:1][C:2]1[C:3]([NH2:27])=[N:4][C:5](=[O:26])[N:6]([CH:25]=1)[C@@H:7]1[O:24][C@H:11]([CH2:12][N:28]=[N+:29]=[N-:30])[C@@H:9]([OH:10])[CH2:8]1

참가 물질

4

반응물 2

HCID 88163Lithium azideHCID 228036685-Iodo-5'-O-p-tolylsulfonyl-2'-deoxycytidine

생성물 1

HCID 30002304-amino-1-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxy-tetrahydrofuran-2-yl]-5-iodo-pyrimidin-2-one수율 65%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A mixture of the compound of Example 1 (2.80 g, 5.52 mmol) and lithium azide (0.41 g, 8.28 mmol) in 30 ml of DMF is heated to 75°-80° (oil bath) for 2 h. The solvent is evaporated to dryness under reduced pressure. The residue is coevaporated several times with ethanol and triturated with ether. The white solid is collected by filtration, washed with ice-cooled water, a small amount of ethanol and ether, and then dried under reduced pressure to afford 1.35 g (65%) of the desired product. An analytical sample is obtained by recrystallization from 95% ethanol; mp 185°-186° (dec); ir (KBr): 4.78 λ (azido).

후처리

  1. temperatureis heated to 75°-80° (oil bath) for 2 h
  2. customThe solvent is evaporated to dryness under reduced pressure
  3. customtriturated with ether
  4. filtrationThe white solid is collected by filtration
  5. washwashed with ice-
  6. temperaturecooled water
  7. dry with materiala small amount of ethanol and ether, and then dried under reduced pressure

출처 및 근거

ORD 기록
ord-fa9b3995342849d599c3b88d3b252919
출처 데이터셋
uspto-grants-1978_06
특허 번호
US04093715

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