Benzophenone [6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]hydrazone → 4-Hydrazino-6-(4-methylpiperazin-1-yl)pyrimidine

HRID 37887Notes

Reaction equation

HRID 37887 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[N:13]=[CH:12][N:11]=[C:10]([NH:14][N:15]=C(C3C=CC=CC=3)C3C=CC=CC=3)[CH:9]=2)[CH2:4][CH2:3]1>Cl>[NH:14]([C:10]1[CH:9]=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[N:13]=[CH:12][N:11]=1)[NH2:15]

Participants

3

Reactant 1

HCID 86672327Benzophenone [6-(4-methylpiperazin-1-yl)pyrimidin-4-yl]hydrazone

Product 1

HCID 133936264-Hydrazino-6-(4-methylpiperazin-1-yl)pyrimidine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

300 mg (808 μmol) of the compound from Example 5A in 15 ml conc. hydrochloric acid are heated at 65° C. for 4 h. After cooling, the reaction mixture is washed with dichloromethane and the aqueous phase is concentrated. This gives 162 mg of the crude product as the hydrochloride. This is stirred with polymer-bound tris-(2-aminoethyl)amine in dichloromethane at RT. After filtration, the filtrate is concentrated and the residue is dried under high vacuum.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture is washed with dichloromethane
  3. concentrationthe aqueous phase is concentrated
  4. filtrationAfter filtration
  5. concentrationthe filtrate is concentrated
  6. customthe residue is dried under high vacuum

Sources & evidence

ORD record
ord-95116dc829d34ebf918587eec942f9d5
Source dataset
uspto-grants-2013_09
Patent number
US08524699B2

Reaction notes

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