N,N,N',N',N'',N''-Hexamethylmethanetriamine → 5,6-Dihydropyrido[2,3-h]quinazolin-2-amine

HRID 34655

Reaction equation

HRID 34655 reaction equation
[N:1]1[C:10]2[CH2:9][CH2:8][CH2:7][C:6](=O)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:12][N:13]([CH:15]([N:19](C)C)[N:16](C)C)C.C(=O)(O)O.NC(N)=N>C1(C)C=CC=CC=1>[N:16]1[C:6]2[C:5]3[CH:4]=[CH:3][CH:2]=[N:1][C:10]=3[CH2:9][CH2:8][C:7]=2[CH:12]=[N:13][C:15]=1[NH2:19]

Participants

5

Reactant 3

HCID 79831N,N,N',N',N'',N''-HexamethylmethanetriamineHCID 286947Carbonic acid-guanidine (1:1)HCID 30168115(6H)-Quinolinone, 7,8-dihydro-

Product 1

HCID 142338515,6-Dihydropyrido[2,3-h]quinazolin-2-amineYield 77%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a refluxing solution, under nitrogen, of 45.0 g (0.306 mol) of 7,8-dihydro-5(6H)-quinolinone, (Example 1), in 750 ml of toluene is added dropwise a solution of 49.8 g (0.343 mol) of tris(dimethylamino)-methane in 250 ml of toluene. The solution is refluxed for 2 hours, cooled and concentrated. The residue is dissolved in 1 l of methanol and treated with 66.2 g (0.367 mol) of guanidine carbonate. The reaction mixture is refluxed, under nitrogen, for 2 hours. The mixture is concentrated to a green solid, the solid is washed with 500 ml of water, filtered and vacuum dried to give 69.1 g of crude product. Recrystallization from acetonitrile affords 6.8 g (77%) of the title compound as a light brown solid; mp 220°-226° C.

Workup

  1. temperatureThe solution is refluxed for 2 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. dissolutionThe residue is dissolved in 1 l of methanol
  5. temperatureThe reaction mixture is refluxed, under nitrogen, for 2 hours
  6. concentrationThe mixture is concentrated to a green solid
  7. washthe solid is washed with 500 ml of water
  8. filtrationfiltered
  9. customvacuum dried
  10. customto give 69.1 g of crude product
  11. customRecrystallization from acetonitrile

Sources & evidence

ORD record
ord-136dcb68c9ac44ea8f5cae799bab2e17
Source dataset
uspto-grants-1988_08
Patent number
US04762843

Linked notes

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