3-(Dimethylamino)-1-phenyl-2-propen-1-one → 7-Phenylpyrazolo[1,5-a]pyrimidine

HRID 1447844

Reaction equation

HRID 1447844 reaction equation
C[N:2]([CH3:13])[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.N[C:15]1[CH:19]=C[NH:17][N:16]=1>C(O)(=O)C>[C:7]1([C:5]2[N:17]3[N:16]=[CH:15][CH:19]=[C:13]3[N:2]=[CH:3][CH:4]=2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 178418806HCID 178418806, compound

Product 1

HCID 200330087-Phenylpyrazolo[1,5-a]pyrimidine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A reaction mixture of 5.25 g. of 3-dimethylaminoacrylophenone [von H. Meerwein et al., Annalen der Chemie, Band 641, 1-39, (1961)] and 2.50 g. of 3-aminopyrazole in 25 ml. of glacial acetic acid is refluxed for 3.5 hours, cooled overnight and evaporated to a thick yellow oil. This oil is dissolved in methylene chloride, washed with a saturated aqueous solution of sodium bicarbonate, dried over sodium sulfate and then passed through a sintered glass funnel or a chromatographic column packed in vacuo with hydrous magnesium silicate. Additional methylene chloride is passed through the funnel (column). The effluent is refluxed on a steam bath. The gradual addition of hexane produces crystals. The crystallization from methylene chloride with hexane is repeated giving the desired product, m.p. 72°-73° C.

Workup

  1. additionA reaction mixture of 5.25 g
  2. temperaturecooled overnight
  3. customevaporated to a thick yellow oil
  4. dissolutionThis oil is dissolved in methylene chloride
  5. washwashed with a saturated aqueous solution of sodium bicarbonate
  6. dry with materialdried over sodium sulfate
  7. custompassed through a sintered glass funnel
  8. temperatureThe effluent is refluxed on a steam bath
  9. additionThe gradual addition of hexane
  10. customproduces crystals
  11. customThe crystallization from methylene chloride with hexane

Sources & evidence

ORD record
ord-9e1c0290e040472386606f5e4feeee2d
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Linked notes

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