Potassium Acetate → Ethyl 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate

HRID 1455087Notes

Reaction equation

[CH2:1]([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][C:11](=CN(C)C)[C:10](=O)[C:9]=2[N:8]([CH3:20])[N:7]=1)=[O:5])[CH3:2].[C:21]([O-])(=O)C.[K+].S(O)(O)(=O)=O.[CH3:31][NH:32][C:33](=[NH:35])[SH:34]>CN(C)C=O>[CH3:20][N:8]1[C:9]2[C:10]3[N:35]=[C:33]([S:34][CH3:21])[N:32]=[CH:31][C:11]=3[CH2:12][CH2:13][C:14]=2[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])=[N:7]1

Participants

Conditions

Temperature: 90 °C

Procedure

9 g (69 mmol) of ethyl-6-[(dimethylamino)methylene]-1-methyl-7-oxo-4,5,6,7-tetrahydro-1H-indazole-3-carboxylate were dissolved in 350 mL of anhydrous dimethylformamide and 13.4 g of anhydrous potassium acetate (138 mmol) and 19.18 g (69 mmol) of methylisothiourea sulfate were added. The mixture was maintained at 90° C. under stirring for 8 hours. The solvent was then evaporated, the residue redissolved with dichloromethane and washed with water. The organic layer was dried over Na2SO4 and evaporated. The crude was finally triturated with diethyl ether and collected by filtration to give 15.5 g (74% yield) of the title compound.

Workup

customThe solvent was then evaporated
dissolutionthe residue redissolved with dichloromethane
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
customevaporated
customThe crude was finally triturated with diethyl ether
filtrationcollected by filtration

Sources & evidence

ORD record: ord-7449390a04194050adaa9c80767eba4b
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482354B2

Reaction notes

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