Water → HCID 86585576, compound

HRID 1355412Notes

Reaction equation

HRID 1355412 reaction equation
[C:1]([N:4]1[C:8]2=[N:9][C:10]3[N:11]([CH3:29])[C:12](=[O:28])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][C@@H:21](OS(C)(=O)=O)[CH3:22])[C:14](=[O:16])[C:15]=3[N:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[N-:30]=[N+:31]=[N-:32].[Na+].O>CS(C)=O>[C:1]([N:4]1[C:8]2=[N:9][C:10]3[N:11]([CH3:29])[C:12](=[O:28])[N:13]([CH2:17][CH2:18][CH2:19][CH2:20][C@H:21]([N:30]=[N+:31]=[N-:32])[CH3:22])[C:14](=[O:16])[C:15]=3[N:7]2[CH2:6][CH2:5]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 86585575HCID 86585575, compound

Product 1

HCID 86585576HCID 86585576, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of (S)-8-acetyl-7,8-dihydro-3-(5-methanesulfonyloxyhexyl)-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (560 mg, 1.28 mmol) and sodium azide (416 mg, 6.4 mmol) in dimethylsulfoxide (5 ml) was stirred at 65° C. for 7 hours. After cooling to room temperature, the reaction mixture was treated with water. After stirring for 1 hour, the solid was filtered, washed with water, and dried under vacuum to provide (R)-8-acetyl-3-(5-azidohexyl)-7,8-dihydro-1-methyl-1H-imidazo[2,1-f]-purine-2,4(3H,6H)-dione (395 mg, 84% yield) as a white powder.

Workup

  1. temperatureAfter cooling to room temperature
  2. stirringAfter stirring for 1 hour
  3. filtrationthe solid was filtered
  4. washwashed with water
  5. customdried under vacuum

Sources & evidence

ORD record
ord-85c750ae3336443fbdcd8c4a6838e661
Source dataset
uspto-grants-2003_07
Patent number
US06586429B2

Reaction notes

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