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

HRID 838928Notes

Reaction equation

HRID 838928 reaction equation
[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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-fa9b3995342849d599c3b88d3b252919
Source dataset
uspto-grants-1978_06
Patent number
US04093715

Reaction notes

Loading…