Water → HCID 131710073, compound

HRID 267214Notes

Reaction equation

HRID 267214 reaction equation
[ClH:1].[CH2:2]([N:4]([C:8]1[NH:13][CH2:12][C:11]2=[C:14]([CH3:20])[N:15]=[C:16]([CH2:17][CH2:18][CH3:19])[N:10]2[N:9]=1)[C:5](=O)[CH3:6])[CH3:3].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>COCCOCCOC.[Pd].CC1C=CC(C(C)C)=CC=1>[ClH:1].[CH2:5]([N:4]([CH2:2][CH3:3])[C:8]1[N:13]=[CH:12][C:11]2=[C:14]([CH3:20])[N:15]=[C:16]([CH2:17][CH2:18][CH3:19])[N:10]2[N:9]=1)[CH3:6]

Participants

8

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 178440028HCID 178440028, compound

Product 1

HCID 131710073HCID 131710073, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 7463P-CymeneSolventHCID 8150DiglymeSolvent

Procedure

N-Ethyl-N-(3,4-dihydro-5-methyl-7-propylimidazo [5,1-f]-as-triazin-2-yl)acetamide, hydrochloride (Example 7) (4.1 g.) and lithium aluminium hydride (3.3 g.) in a mixture of dimethyl digol (130 ml.) and diethyl digol (150 ml.) were heated under reflux for 24 hours and cooled. Water (3.37 ml.) was added followed by aqueous sodium hydroxide (3.3 ml.) and water (9.8 ml.). The solid was filtered off and the filtrate was evaporated. The residue was chromatographed on active alumina (300 g.) using ethyl acetate as eluent. The first 400 ml. of eluate was discarded and a fraction (900 ml.) then collected was evaporated to give an oil. This oil (1.1 g.) and palladium on charcoal catalyst (1 g., 10%) in p-cymene (60 ml.) were heated under reflux for 30 minutes, cooled and filtered. The filtrate was shaken with 2N hydrochloric acid (3 × 25 ml.) and the aqueous acid solution was separated and neutralised by addition of potassium carbonate. The mixture was extracted with ethyl acetate and the extracts were dried over magnesium sulphate, filtered and evaporated. The residue in ether was treated with a solution of hydrogen chloride in anhydrous ether. The solid crystallised from a mixture of ethyl acetate and ether to give the product, m.p. 83°-84°.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 24 hours
  3. temperaturecooled
  4. filtrationThe solid was filtered off
  5. customthe filtrate was evaporated
  6. customThe residue was chromatographed on active alumina (300 g.)
  7. customa fraction (900 ml.) then collected
  8. customwas evaporated
  9. customto give an oil
  10. temperatureunder reflux for 30 minutes
  11. temperaturecooled
  12. filtrationfiltered
  13. customthe aqueous acid solution was separated
  14. additionneutralised by addition of potassium carbonate
  15. extractionThe mixture was extracted with ethyl acetate
  16. dry with materialthe extracts were dried over magnesium sulphate
  17. filtrationfiltered
  18. customevaporated
  19. additionThe residue in ether was treated with a solution of hydrogen chloride in anhydrous ether
  20. customThe solid crystallised from a mixture of ethyl acetate and ether
  21. customto give the product, m.p. 83°-84°

Sources & evidence

ORD record
ord-13b552e54eb3444e9dbf861b9d73d4d1
Source dataset
uspto-grants-1976_03
Patent number
US03941785

Reaction notes

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