1,8-Diazabicyclo(5.4.0)undec-7-ene → 5-Amino-2-(2-furyl)-7-(4-(2-hydroxy-2-methylpropyl)piperazinyl)[1,2,4]triazolo[1,5-c]pyrimidine

HRID 1264874Notes

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.C1CCN2C(=NCCC2)CC1.[OH:28][C:29]([CH3:38])([CH3:37])[CH2:30][N:31]1[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]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:34]2[CH2:35][CH2:36][N:31]([CH2:30][C:29]([OH:28])([CH3:37])[CH3:38])[CH2:32][CH2:33]2)[N:3]=1

Participants

Conditions

Temperature: 140 °C

Procedure

Into 7 mL of DMSO, 500 mg (2.12 mmol) of Compound E was dissolved, and then 0.95 mL (6.36 mmol) of DBU and 1.50 g (9.50 mmol) of 1-(2-hydroxy-2-methylpropyl)piperazine were added thereto, followed by stirring at 140° C. for about 2 hours. After completion of the reaction, the reaction mixture was extracted by adding chloroform and water, and 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 (3% methanol-chloroform) and then recrystallized from a mixed solvent of hexane-ethyl acetate to obtain 250 mg of Compound 1 as a white solid (yield: 33%).

Workup

customAfter completion of the reaction
extractionthe reaction mixture was extracted
additionby adding chloroform and water
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 (3% methanol-chloroform)
customrecrystallized from a mixed solvent of hexane-ethyl acetate

Sources & evidence

ORD record: ord-e2148aa9fbf54eeebc9d8a6054e8592c
Source dataset: uspto-grants-2003_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06545000B1

Reaction notes

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