Potassium Carbonate → Ethyl 8-methoxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 875105Notes

Reaction equation

HRID 875105 reaction equation
C[N:2]([CH:4]=[C:5]1[C:13](=O)[C:12]2[N:11]([CH3:15])[N:10]=[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:8]=2[CH2:7][CH2:6]1)[CH3:3].S(O)(O)(=O)=O.C[NH:27]C(=N)O.[C:31](=[O:34])([O-])[O-].[K+].[K+]>C(#N)C>[CH3:31][O:34][C:3]1[N:2]=[CH:4][C:5]2[CH2:6][CH2:7][C:8]3[C:9]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[N:10][N:11]([CH3:15])[C:12]=3[C:13]=2[N:27]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 67075650ethyl 6-[(dimethylamino)methylene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylateHCID 178485200HCID 178485200, compound

Product 1

HCID 45141796Ethyl 8-methoxy-1-methyl-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylateYield 86%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.0 g (7.2 mmol) of ethyl 6-[(dimethylamino)methylene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate were dissolved in 200 mL of acetonitrile and 17.4 g (70.6 mmol) of methylisourea sulfate and 10.0 g (72.4 mmol) of potassium carbonate were added. The reaction mixture was stirred at reflux for 16 hours. The solvent was then evaporated, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over anhydrous Na2SO4 and concentrated. After a chromatography on a silica gel column (eluant dichloromethane) 1.7 g of product were obtained (86% yield).

Workup

  1. temperatureat reflux for 16 hours
  2. customThe solvent was then evaporated
  3. dissolutionthe residue redissolved with dichloromethane
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous Na2SO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-c750c93489f44bebbcb34b3e543671e6
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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