2-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)- → 2-Methyl-7-(4-pyridinyl)pyrazolo(1,5-a) pyrimidine-3-carbonitrile

HRID 1681137Notes

Reaction equation

HRID 1681137 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([CH3:7])[C:3]=1[C:8]#[N:9].CN(C)[CH:12]=[CH:13][C:14]([C:16]1[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=1)=O>C(O)(=O)C>[CH3:7][C:4]1[C:3]([C:8]#[N:9])=[C:2]2[N:1]=[CH:12][CH:13]=[C:14]([C:16]3[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=3)[N:6]2[N:5]=1

Participants

4

Reactant 2

HCID 7145312-Propen-1-one, 3-(dimethylamino)-1-(4-pyridinyl)-HCID 178434678HCID 178434678, compound

Product 1

HCID 150420792-Methyl-7-(4-pyridinyl)pyrazolo(1,5-a) pyrimidine-3-carbonitrileYield 52.5%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 6.1 g of 5-amino-3-methyl-4-pyrazole carbonitrile and 8.81 g of 3-dimethylamino-1-(4-pyridinyl)-2-propen-1-one in 50 ml of glacial acetic acid is stirred and heated at reflux for 5 hours. The reaction mixture is cooled and the precipitate which forms is collected by filtration and washed with water and a little dichloromethane to give a solid. The solid is partitioned between saturated sodium bicarbonate and dichloromethane. The organic layer is dried over anhydrous sodium sulfate and passed through a short column of hydrous magensium silicate. The addition of hexane to the eluate crystallizes the product which is collected by filtration to give 6.17 g of the desired product, mp 220°-221° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for 5 hours
  3. temperatureThe reaction mixture is cooled
  4. filtrationthe precipitate which forms is collected by filtration
  5. washwashed with water
  6. customa little dichloromethane to give a solid
  7. customThe solid is partitioned between saturated sodium bicarbonate and dichloromethane
  8. dry with materialThe organic layer is dried over anhydrous sodium sulfate
  9. additionThe addition of hexane to the eluate
  10. customcrystallizes the product which
  11. filtrationis collected by filtration

Sources & evidence

ORD record
ord-1e3c776a09f54e648e8854f381d0651a
Source dataset
uspto-grants-1992_12
Patent number
US05169850

Reaction notes

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