Lithium azide → HCID 19757676, compound

HRID 1587280Notes

Reaction equation

HRID 1587280 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].Cl[C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[NH:10][CH:11]=[N:12]2.[N-:17]=[N+:18]=[N-:19].[Li+]>CS(C)=O>[NH:1]1[CH2:5][CH2:4][CH2:3][C:2]1=[O:6].[N:17]([C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[NH:10][CH:11]=[N:12]2)=[N+:18]=[N-:19]

Participants

4

Reactant 2

HCID 88163Lithium azideHCID 19757659HCID 19757659, compound

Product 1

HCID 19757676HCID 19757676, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

The 6-chloropurine pyrrolidone (1 mmol) is treated with lithium azide (2 mmol) in dimethyl sulfoxide (2 ml) at 30°-100° C. for several h. At the end of this time the mixture is evaporated under reduced pressure, dissolved in chloroform, washed with 10% sodium bicarbonate, and the organic layer dried over sodium sulfate and concentrated under reduced pressure. The residue is chromatographed on silica using a gradient of methanol in chloroform (0-25%).

Workup

  1. customAt the end of this time the mixture is evaporated under reduced pressure
  2. dissolutiondissolved in chloroform
  3. washwashed with 10% sodium bicarbonate
  4. dry with materialthe organic layer dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue is chromatographed on silica using a gradient of methanol in chloroform (0-25%)

Sources & evidence

ORD record
ord-ada4bf8bc27846f58152b9e1e0f36e09
Source dataset
uspto-grants-1993_06
Patent number
US05217866

Reaction notes

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