Isopropanol → HCID 13686024, compound

HRID 1380525Notes

Reaction equation

HRID 1380525 reaction equation
[N:1]1([C:7]2[N:21]=[C:10]3[N:11]=[CH:12][CH:13]=[C:14]([C:15]4[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=4)[N:9]3[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH:23]([CH3:32])[C:24]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:25].CC(O)C>C(N(CC)CC)C>[C:26]1([C:24](=[O:25])[CH:23]([N:4]2[CH2:3][CH2:2][N:1]([C:7]3[N:21]=[C:10]4[N:11]=[CH:12][CH:13]=[C:14]([C:15]5[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=5)[N:9]4[N:8]=3)[CH2:6][CH2:5]2)[CH3:32])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 164522-BromopropiophenoneHCID 13686022HCID 13686022, compound

Product 1

HCID 13686024HCID 13686024, compoundYield 27.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

A mixture of 5.6 g (0.02 moles) of 2-(1-piperazinyl)-7-(4-pyridyl)[1,2,4]triazolo[1,5-a]pyrimidine (prepared as described in Example 47) and 4.2 g (0.02 moles) of α-bromopropiophenone in 100 ml of 2-propanol containing 3.6 ml (0.026 moles) of triethylamine was heated at the reflux temperature for 24 hours. The reaction mixture was evaporated to dryness in vacuo. Then 100 ml of water was added to the residue and the mixture was extracted three times with a total of 100 ml of chloroform. The combined extracts were dried over magnesium sulfate and filtered. The filtrate was passed through a pad of magnesium silicate, washing with chloroform. The filtrate was evaporated to a syrup. The syrup was dissolved in 20 ml of ethanol and 200 ml of diethyl ether was added, then hexane was added until cloudy. The mixture was evaporated by boiling to about 100 ml, then was cooled and filtered to collect the precipitate, which was washed with ether and gave 2.3 g of the desired product as yellow crystals, mp 142°-144° C.

Workup

  1. temperaturewas heated at the reflux temperature for 24 hours
  2. customThe reaction mixture was evaporated to dryness in vacuo
  3. additionThen 100 ml of water was added to the residue
  4. extractionthe mixture was extracted three times with a total of 100 ml of chloroform
  5. dry with materialThe combined extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. washwashing with chloroform
  8. customThe filtrate was evaporated to a syrup
  9. dissolutionThe syrup was dissolved in 20 ml of ethanol
  10. addition200 ml of diethyl ether was added
  11. additionhexane was added until cloudy
  12. customThe mixture was evaporated
  13. temperaturewas cooled
  14. filtrationfiltered
  15. customto collect the precipitate, which
  16. washwas washed with ether

Sources & evidence

ORD record
ord-3d217e5232e648ebbdcba3ed09fb7cc2
Source dataset
uspto-grants-1986_04
Patent number
US04582833

Reaction notes

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