Cyanogen Bromide → HCID 135767478, compound

HRID 1762076Notes

Reaction equation

HRID 1762076 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]1[N:11]=[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:9][N:8]=1.[N:18]#[C:19]Br>CO>[NH2:4][C:5]1[N:6]2[N:18]=[CH:19][N:1]=[C:2]2[C:3]2[NH:9][C:10]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)=[N:11][C:7]=2[N:8]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 178509097HCID 178509097, compound

Product 1

HCID 135767478HCID 135767478, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
40 °C

Procedure

A mixture of 3-(5-aminoimidazol-4-yl)-5-phenyl-1,2,4-triazole (11.3 g, from Example 1), methanol (200 mL) and cyanogen bromide (5.25 g) is stirred under nitrogen for 2 hours at 40° C. It is cooled and the solid collected, dissolved in 10N Sodium hydroxide solution, filtered and precipitated by addition of glacial acetic acid to pH 5. The solid is washed with water, stirred in a mixture of methanesulphonic acid in methanol for one-half hour and collected (1.39 g), mp >350°. After drying at room temperature and high vacuum, the hemihydrate of 5-amino-2-phenyl-[1,2,4]triazolo[5,1-i]purine is thus obtained.

Workup

  1. temperatureIt is cooled
  2. customthe solid collected
  3. dissolutiondissolved in 10N Sodium hydroxide solution
  4. filtrationfiltered
  5. customprecipitated by addition of glacial acetic acid to pH 5
  6. washThe solid is washed with water
  7. stirringstirred in a mixture of methanesulphonic acid in methanol for one-half hour
  8. customcollected (1.39 g), mp >350°
  9. customAfter drying at room temperature

Sources & evidence

ORD record
ord-141823d979d64c31bbc7509e2841c353
Source dataset
uspto-grants-1989_05
Patent number
US04831013

Reaction notes

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