Chloromethyl Methyl Ether → HCID 23084861, compound

HRID 1783294Notes

Reaction equation

[CH3:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7](=[O:15])[NH:6][C:5]=2[N:4]([CH3:16])[N:3]=1.[H-].[Na+].[CH3:19][O:20][CH2:21]Cl>CS(C)=O>[CH3:1][C:2]1[C:14]2[C:13]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:7]([O:15][CH2:19][O:20][CH3:21])=[N:6][C:5]=2[N:4]([CH3:16])[N:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

1,3-Dimethyl-3H-pyrazolo[3,4-c]isoquinolin-5(4H)-one (10 g) was suspended in dimethylsulfoxide (100 mL), and sodium hydride (60%, 2.1 g) was added at room temperature. The mixture was stirred with heating at 70° C. for 2 hrs, and cooled to room temperature. Chloromethyl methyl ether (4.6 mL) was added, and the mixture was stirred at room temperature for 30 min. After the completion of the reaction, the reaction mixture was poured into ice-water, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over magnesium sulfate, and the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1) to give 1,3-dimethyl-5-methoxymethoxy-3H-pyrazolo[3,4-c]isoquinoline (10.6 g).

Workup

temperaturecooled to room temperature
stirringthe mixture was stirred at room temperature for 30 min
customAfter the completion of the reaction
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over magnesium sulfate
customthe solvent was evaporated
customThe obtained residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record: ord-f2e54bf2162441c3ba25b67ddacf4642
Source dataset: uspto-grants-2009_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07501412B2

Reaction notes

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