Piperazine → HCID 22378671, compound

HRID 895487Notes

Reaction equation

HRID 895487 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:3]=1.[NH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])O.[Na+]>CS(C)=O>[C:8]1([C:6]2[N:5]=[C:4]([NH:14][CH2:15][CH2:16][NH:17][C:18](=[O:20])[CH3:19])[CH:3]=[C:2]([N:21]3[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]3)[N:7]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

5

Reactant 3

HCID 4837PiperazineHCID 516892Sodium BicarbonateHCID 22378694HCID 22378694, compound

Product 1

HCID 22378671HCID 22378671, compoundYield 49.3%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
110 °C

Procedure

N-{2-[(6-Chloro-2-phenylpyrimidin-4-yl)amino]ethyl}acetamide (27) (1.5 g) and piperazine (4.44 g) were dissolved in DMSO. To this was added sodium hydrogencarbonate (2.16 g) and the mixture heated to 110° C. for 3 hrs. The reaction mixture was cooled to ambient temperature then partitioned between ethyl acetate (150 ml) and water (150 ml). The aqueous layer was washed with ethyl acetate (2×200 ml) and the combined organics washed with brine (100 ml), dried over magnesium sulfate then filtered. Removal of the solvent in vacuo furnished the title compound (0.865 g).

Workup

  1. temperatureThe reaction mixture was cooled to ambient temperature
  2. customthen partitioned between ethyl acetate (150 ml) and water (150 ml)
  3. washThe aqueous layer was washed with ethyl acetate (2×200 ml)
  4. washthe combined organics washed with brine (100 ml)
  5. dry with materialdried over magnesium sulfate
  6. filtrationthen filtered
  7. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-d157160f36a449f0a5ecf69097aad68d
Source dataset
uspto-grants-2005_07
Patent number
US06916804B2

Reaction notes

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