Ethyl 8-[(aminocarbonyl)amino]-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate → 8-[(aminocarbonyl)amino]-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide
Reaction equation
[NH2:1][C:2]([NH:4][C:5]1[N:14]=[CH:13][C:12]2[CH:11]=[CH:10][C:9]3[C:15]([C:19]([O:21]CC)=O)=[N:16][N:17]([CH3:18])[C:8]=3[C:7]=2[N:6]=1)=[O:3].CO.C[N:27](C)C=O.[OH-].[NH4+]>>[NH2:1][C:2]([NH:4][C:5]1[N:14]=[CH:13][C:12]2[CH:11]=[CH:10][C:9]3[C:15]([C:19]([NH2:27])=[O:21])=[N:16][N:17]([CH3:18])[C:8]=3[C:7]=2[N:6]=1)=[O:3]Participants
3
Conditions
- Temperature
- 65 °C
Procedure
A suspension of 0.20 g (0.63 mmol) of ethyl 8-[(aminocarbonyl)amino]-1-methyl-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate in 15 mL of a mixture methanol/dimethylformamide/ammonium hydroxide 30% 1/1/1 was stirred in a close bottle at 65° C. for 48 hours. The solvent was then evaporated under reduced pressure, the residue redissolved with a mixture dichloromethane/methanol 9/1 and washed with water. The organic layer was dried over anhydrous Na2SO4 and evaporated to dryness. The product was purified by chromatography on a silica gel column (eluant dichloromethane/acetone/methanol) giving 0.09 g (50% yield) of the title compound.
Workup
- customThe solvent was then evaporated under reduced pressure
- dissolutionthe residue redissolved with a mixture dichloromethane/methanol 9/1
- washwashed with water
- dry with materialThe organic layer was dried over anhydrous Na2SO4
- customevaporated to dryness
- customThe product was purified by chromatography on a silica gel column (eluant dichloromethane/acetone/methanol)
Sources & evidence
- ORD record
- ord-3e06fbc7590f4fd0a0c12c83d9f46b98
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08981089B2
Reaction notes
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