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

HRID 838928ノート

反応式

HRID 838928 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-fa9b3995342849d599c3b88d3b252919
出典データセット
uspto-grants-1978_06
特許番号
US04093715

反応ノート

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