Phthalic Anhydride → HCID 136355660, compound

HRID 2200917Notes

Reaction equation

HRID 2200917 reaction equation
[NH2:1][C:2]1[N:21]=[C:5]2[NH:6][C:7]([CH3:20])=[C:8]([C:18]#[N:19])[CH:9]([C:10]3[CH:15]=[CH:14][C:13]([C:16]#[N:17])=[CH:12][CH:11]=3)[N:4]2[N:3]=1.[C:22]1(=O)[O:27][C:25](=[O:26])[C:24]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:23]12.C(N(CC)CC)C>C1(C)C=CC=CC=1.N1C=CC=CC=1>[C:16]([C:13]1[CH:12]=[CH:11][C:10]([CH:9]2[N:4]3[N:3]=[C:2]([N:1]4[C:25](=[O:26])[C:24]5[C:23](=[CH:31][CH:30]=[CH:29][CH:28]=5)[C:22]4=[O:27])[N:21]=[C:5]3[NH:6][C:7]([CH3:20])=[C:8]2[C:18]#[N:19])=[CH:15][CH:14]=1)#[N:17]

Participants

6

Reactant 3

HCID 6811Phthalic Anhydride2×HCID 8471Triethylamine2×HCID 136355661HCID 136355661, compound

Product 1

HCID 136355660HCID 136355660, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolvent2×HCID 1140TolueneSolvent

Procedure

Under argon, (rac)-2-amino-7-(4-cyanophenyl)-5-methyl-4,7-dihydro[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitrile (15 g, 54.1 mmol) together with phthalic anhydride (11.22 g, 75.7 mmol, 1.4 eq.) was suspended in a mixture of toluene (500 ml) and pyridine (600 ml), triethylamine (1.51 ml, 10.8 mmol, 0.2 eq.) was added and the mixture was heated under reflux overnight. More pyridine (200 ml), phthalic anhydride (8 g, 54.0 mmol, 1.0 eq.) and triethylamine (1.51 ml, 10.8 mmol, 0.2 eq.) were then added, and the mixture was heated under reflux for another 12 h. The reaction mixture was then concentrated under reduced pressure and the residue was dried under high vacuum (12 h). Three times, the crude product was suspended in ethanol (100 ml), stirred for 1 h, filtered off, washed with pentane and dried under high vacuum. The product obtained was a light-beige solid (20 g), which was recrystallised from DMF/methanol. To this end, the solid was initially dissolved in hot DMF (250 ml, 150° C.) and the cold DMF solution was then slowly, with stirring, poured into methanol (1.3 liters), whereupon the product precipitated out. The precipitate was filtered off and dried under high vacuum. Reprecipitation from DMF/methanol gave 15.91 g (99% pure, 71.5% of theory) of the title compound.

Workup

  1. additionwas added
  2. temperaturethe mixture was heated
  3. temperatureunder reflux overnight
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for another 12 h
  6. concentrationThe reaction mixture was then concentrated under reduced pressure
  7. customthe residue was dried under high vacuum (12 h)
  8. filtrationfiltered off
  9. washwashed with pentane
  10. customdried under high vacuum
  11. customThe product obtained
  12. customwas recrystallised from DMF/methanol
  13. dissolutionTo this end, the solid was initially dissolved in hot DMF (250 ml, 150° C.)
  14. stirringslowly, with stirring
  15. additionpoured into methanol (1.3 liters), whereupon the product
  16. customprecipitated out
  17. filtrationThe precipitate was filtered off
  18. customdried under high vacuum
  19. customReprecipitation from DMF/methanol

Sources & evidence

ORD record
ord-ea27d8309792412787af3e9608ef5a42
Source dataset
uspto-grants-2016_06
Patent number
US09359362B2

Reaction notes

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