Hydrazinium chloride → HCID 21948510, compound

HRID 2214783Notes

Reaction equation

HRID 2214783 reaction equation
Cl.[NH2:2]N.C[N:5](C)/[CH:6]=[C:7](\[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)/[C:8]([C:10]1[CH:15]=[CH:14][N:13]=[C:12]([S:16][CH3:17])[N:11]=1)=O>C(O)C>[CH3:17][S:16][C:12]1[N:11]=[C:10]([C:8]2[NH:2][N:5]=[CH:6][C:7]=2[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 115031Hydrazinium chlorideHCID 58699952HCID 58699952, compound

Product 1

HCID 21948510HCID 21948510, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine hydrochloride (78 mg, 1.13 mmol, 1.5 equiv) was added to a solution of (2E)-3-(dimethylamino)-1-[2-(methylthio)pyrimidin-4-yl]-2-phenylprop-2-en-1-one(3-2, 226 mg, 0.76 mmol, 1 equiv) in ethanol (10 mL). The solution was refluxed for 3 hours and concentrated. The residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution. The organic layer was dried over magnesium sulfate and concentrated to give 2-(methylthio)-4-(4-phenyl-1H-pyrazol-5-yl)pyrimidine (3-3) as a tan colored gum.

Workup

  1. temperatureThe solution was refluxed for 3 hours
  2. concentrationconcentrated
  3. customThe residue was partitioned between ethyl acetate and saturated sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-59aced37efc74726a2587c8ec37919e7
Source dataset
uspto-grants-2006_09
Patent number
US07109204B2

Reaction notes

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