Dimethylformamide → 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44600Notes

Reaction equation

HRID 44600 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:12]([C:16]([O:18]CC)=O)=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1.C[N:22](C)C=O.[NH4+].[OH-]>CO>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[CH:8]=[CH:7][C:6]3[C:12]([C:16]([NH2:22])=[O:18])=[N:13][N:14]([CH3:15])[C:5]=3[C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 57444093Ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

Product 1

HCID 574441008-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamideYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

2.5 g of ethyl 8-amino-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate (9.16 mmol) were dissolved in 40 mL of methanol, 40 mL of dimethylformamide and 50 mL of NH4OH 30% mixture. The mixture was maintained at 65° C. under stirring for a day. The solvent was then evaporated to dryness, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated. The crude was triturated with diethyl ether and the product collected by filtration (50% yield).

Workup

  1. customThe solvent was then evaporated to dryness
  2. dissolutionthe residue redissolved with dichloromethane
  3. washwashed with water
  4. dry with materialThe organic layer was dried over Na2SO4
  5. customevaporated
  6. customThe crude was triturated with diethyl ether
  7. filtrationthe product collected by filtration (50% yield)

Sources & evidence

ORD record
ord-fe63789c4a2047d6a979ae178973f972
Source dataset
uspto-grants-2013_09
Patent number
US08541429B2

Reaction notes

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