Piperazine → 5-Amino-2-(2-furyl)-7-piperazinyl[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264873Notes

Reaction equation

[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4](Cl)[N:3]=1.[NH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>CS(C)=O>[NH2:1][C:2]1[N:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[N:10]=[C:6]2[CH:5]=[C:4]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

Into 180 mL of DMSO, 10.5 g (44.6 mmol) of Compound E and 19.2 g (223 mmol) of piperazine were dissolved, followed by stirring at 150° C. for about 2 hours. After completion of the reaction, the solvent was evaporated under reduced pressure, water was added to the residue, and the mixture was extracted with chloroform. The organic layer was washed with water and brine, and then dried over anhydrous magnesium sulfate. After evaporation of the solvent, the resulting residue was purified by silica gel column chromatography (23% aqueous ammonia/methanol/chloroform=1/10/90) and then recrystallized from ethyl acetate to obtain 9.91 g of Compound F as a white solid (yield: 78%).

Workup

customAfter completion of the reaction
customthe solvent was evaporated under reduced pressure, water
additionwas added to the residue
extractionthe mixture was extracted with chloroform
washThe organic layer was washed with water and brine
dry with materialdried over anhydrous magnesium sulfate
customAfter evaporation of the solvent
customthe resulting residue was purified by silica gel column chromatography (23% aqueous ammonia/methanol/chloroform=1/10/90)
customrecrystallized from ethyl acetate

Sources & evidence

ORD record: ord-4ed4e073b107416ca31cf42e55bf4ca8
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545000B1

Reaction notes

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