Diisopropylethylamine → 2-Phenyl-5,6-dihydro-1,2,4-triazolo[4,3-c]quinazolin-3-one

HRID 618654Notes

Reaction equation

HRID 618654 reaction equation
Cl[C:2]1[N:11]2[C:12](=[O:21])[N:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:14]=[C:10]2[C:9]2[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=2[N:3]=1.C(N(CC)C(C)C)(C)C>C(O)C.C(Cl)(Cl)Cl.[Pd]>[C:15]1([N:13]2[C:12](=[O:21])[N:11]3[CH2:2][NH:3][C:4]4[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=4[C:10]3=[N:14]2)[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1

Participants

6

Reactant 2

HCID 81531DiisopropylethylamineHCID 15428837HCID 15428837, compound

Product 1

HCID 1354844832-Phenyl-5,6-dihydro-1,2,4-triazolo[4,3-c]quinazolin-3-one

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 6212ChloroformSolvent

Procedure

A mixture of 5-chloro-2-phenyl-1,2,4triazolo[4,3-c]-quinazolin-3-one (1g, 3.4 mmol), N,N-diisopropylethylamine (1 ml, 6.7 mmol) and 10% Pd-C (200 mg) in ethanol was shaken under hydrogen at 50 psi overnight. The reaction was diluted with CHCl3 and filtered through Celite. The filtrate was evaporated under reduced pressure and the residue dissolved in dichloromethane. The solution was washed with water, dried over Na2SO4 and evaporated under reduced pressure to yield 2-phenyl-5,6-dihydro-1,2,4-triazolo[4,3-c]quinazolin-3-one (Compound 2) as a white solid. m.p. 202-204° C.

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated under reduced pressure
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe solution was washed with water
  5. dry with materialdried over Na2SO4
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-ec76034a071d43b4b2688d3127f86ba5
Source dataset
uspto-grants-1999_09
Patent number
US05955465

Reaction notes

Loading…