Dimethylformamide → 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxamide

HRID 44580Notes

Reaction equation

[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15][CH3:16])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:17]([O:19]CC)=O)=[N:3]1.C[N:23](C)C=O.O.[NH4+]>CO>[CH3:1][N:2]1[C:14]2[C:13]3[N:12]=[C:11]([S:15][CH3:16])[N:10]=[CH:9][C:8]=3[CH2:7][CH2:6][C:5]=2[C:4]([C:17]([NH2:23])=[O:19])=[N:3]1

Participants

Conditions

Temperature: 65 °C

Procedure

13.00 g (0.043 mol) of ethyl 1-methyl-8-(methylthio)-4,5-dihydro-1H-pyrazolo[4,3-h]quinazoline-3-carboxylate were suspended in a mixture of 200 mL of methanol, 200 mL of dimethylformamide and 200 mL of ammonium hydrate 30%. The mixture was stirred at 65° C. in a closed bottle for about 8 hours. 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 purified by chromatography on a silica gel column eluted by a mixture cyclohexane/ethyl acetate, giving 6.16 g (52% yield) of the title compound.

Workup

customThe solvent was then evaporated to dryness
dissolutionthe residue redissolved with dichloromethane
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
customevaporated
customThe crude was purified by chromatography on a silica gel column
washeluted by a mixture cyclohexane/ethyl acetate

Sources & evidence

ORD record: ord-9280bad6438c4dc69322747c096c17b0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541429B2

Reaction notes

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