Triethylamine → HCID 178503424, compound

HRID 2359029Notes

Reaction equation

HRID 2359029 reaction equation
C[N:2](C)[CH:3]=[C:4]([C:13]1[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=1)[C:5]([C:7]1[S:8][C:9]([Cl:12])=[CH:10][CH:11]=1)=O.O.NN.C([N:27](CC)CC)C>C(O)C.O>[Cl:12][C:9]1[S:8][C:7]([C:5]2[C:4]([C:13]3[CH:18]=[CH:17][N:16]=[C:15]([S:19][CH3:20])[N:14]=3)=[CH:3][NH:2][N:27]=2)=[CH:11][CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 24654Hydrazine hydrate (1:1)HCID 67261197HCID 67261197, compound

Product 1

HCID 178503424HCID 178503424, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a mixture of 3-(dimethylamino)-1-(5-chloro-2-thienyl)-2-[2-(methylsulfanyl)pyrimidin-4-yl]prop-2-en-1-one (1 eq, 96 mmol) in 300 mL ethanol was added dropwise hydrazine hydrate (1.5 eq, 144 mmol) and then triethylamine (1.5 eq, 144 mmol). The mixture was heated under reflux for 2 h and then overnight at room temperature. The solvent was then slowly poured in 1 L of water. The resulting precipitate was filtered and dried to afford 24 g of 4-[3-(5-chloro-2-thienyl)-1H-pyrazol-4-yl]-2-(methylsulfanyl)pyrimidine (80% yield).

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 2 h
  3. customovernight
  4. customat room temperature
  5. filtrationThe resulting precipitate was filtered
  6. customdried

Sources & evidence

ORD record
ord-1a365012950c44fc84e93bc8fdf2f431
Source dataset
uspto-grants-2014_04
Patent number
US08685974B2

Reaction notes

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