Hydrazine hydrate (1:1) → 4-(4-Cyclobutylpiperazin-1-yl)-6-hydrazinopyrimidine

HRID 562452Notes

Reaction equation

O.[NH2:2][NH2:3].Cl[C:5]1[CH:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH:17]3[CH2:20][CH2:19][CH2:18]3)[CH2:13][CH2:12]2)[N:8]=[CH:7][N:6]=1>C(O)C>[CH:17]1([N:14]2[CH2:15][CH2:16][N:11]([C:9]3[CH:10]=[C:5]([NH:2][NH2:3])[N:6]=[CH:7][N:8]=3)[CH2:12][CH2:13]2)[CH2:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 80 °C

Procedure

At RT, 4.4 ml (4.5 g, 89.7 mmol) of hydrazine hydrate are added dropwise with stirring to a solution of 1.9 g (7.5 mmol) of 4-chloro-6-(4-cyclobutylpiperazin-1-yl)pyrimidine in 28 ml of ethanol. The reaction solution is stirred at 80° C. for 16 h. For work-up, the mixture is concentrated under reduced pressure, the residue is triturated repeatedly with diethyl ether, and the precipitated solid is filtered off and dried under reduced pressure. The residue is then purified by column chromatography on silica gel (mobile phase dichloromethane/methanol 10/2). Yield: 1.5 g (80% of theory)

Workup

concentrationFor work-up, the mixture is concentrated under reduced pressure
customthe residue is triturated repeatedly with diethyl ether
filtrationthe precipitated solid is filtered off
customdried under reduced pressure
customThe residue is then purified by column chromatography on silica gel (mobile phase dichloromethane/methanol 10/2)

Sources & evidence

ORD record: ord-e983cb9e25bb487e93f3de2224459ecd
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067407B2

Reaction notes

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