Cyanogen Bromide → HCID 14458863, compound

HRID 1762077Notes

Reaction equation

HRID 1762077 reaction equation
[H-].[Na+].[NH2:3][C:4]1[C:9]([C:10]2[N:14]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[NH:12][N:11]=2)=[N:8][CH:7]=[CH:6][N:5]=1.[N:20]#[C:21]Br>CN(C)C=O>[NH2:20][C:21]1[N:11]2[N:12]=[C:13]([C:15]3[O:16][CH:17]=[CH:18][CH:19]=3)[N:14]=[C:10]2[C:9]2[N:8]=[CH:7][CH:6]=[N:5][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 10476Cyanogen BromideHCID 24758Sodium hydrideHCID 14458805HCID 14458805, compound

Product 1

HCID 14458863HCID 14458863, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 50% sodium hydride in oil (300 mg) in dry dmethylformamide (16 ml) is added 3-(2-aminopyrazin-3-yl)-5-(2-furyl)-1,2,4-triazole (1.37 g) and the whole stirred under nitrogen at 60° until a solution forms. To this is added cyanogen bromide (700 mg) in dimethylformamide (9 ml) and the whole stirred under nitrogen over 66 hours at 60°. It is cooled to 0° and the solid collected, washed with dimethylformamide, then water, then ethanol and finally ether and air dried. It is recrystallized from dimethylacetamide (70 ml) to which methanol (50 ml) is added to form pure 5-amino-(2-furyl)-pyrazino[2,3-e][1,2,4]-triazolo[1,5-c]pyrimidine, melting in the range 347°-351°.

Workup

  1. stirringthe whole stirred under nitrogen over 66 hours at 60°
  2. temperatureIt is cooled to 0°
  3. customthe solid collected
  4. washwashed with dimethylformamide
  5. dry with materialwater, then ethanol and finally ether and air dried
  6. customIt is recrystallized from dimethylacetamide (70 ml) to which methanol (50 ml)
  7. additionis added

Sources & evidence

ORD record
ord-923b0cb3edf248329b99d924024b1ec5
Source dataset
uspto-grants-1989_05
Patent number
US04831013

Reaction notes

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