3-(Dimethylamino)-1-phenyl-2-propen-1-one → Ethyl 4-phenylimidazolo[1,5-a]pyrimidine-8-carboxylate

HRID 225278Notes

Reaction equation

HRID 225278 reaction equation
[NH2:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8].CN(C)[CH:14]=[CH:15][C:16]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=O>C(O)(=O)C>[C:18]1([C:16]2[N:6]3[CH:5]=[N:4][C:3]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[C:2]3[N:1]=[CH:14][CH:15]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 178470302HCID 178470302, compound

Product 1

HCID 23329848Ethyl 4-phenylimidazolo[1,5-a]pyrimidine-8-carboxylate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 1.55 g. of ethyl 5-aminoimidazole-4-carboxylate and 1.75 g. of 3-dimethylaminoacrylophenone in 25 ml. glacial acetic acid is refluxed for 6 hours and when cooled no precipitate formed. The reaction is evaporated to dryness and dissolved in methylene chloride. After being washed with a saturated sodium bicarbonate solution and dried with anhydrous sodium sulfate, the solution was passed through a short column of hydrous magnesium silicate. Hexane addition to this solution gave the desired product, m.p. 200°-204° C.

Workup

  1. additionA mixture of 1.55 g
  2. temperaturewhen cooled no precipitate
  3. customformed
  4. customThe reaction is evaporated to dryness
  5. dissolutiondissolved in methylene chloride
  6. washAfter being washed with a saturated sodium bicarbonate solution
  7. dry with materialdried with anhydrous sodium sulfate
  8. additionHexane addition to this solution

Sources & evidence

ORD record
ord-d31ae625f7f94cf1b3470e3e1fda0210
Source dataset
uspto-grants-1980_11
Patent number
US04236005

Reaction notes

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