Water → 3-Desmethyl Istradefylline

HRID 375368Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:23]=[CH:24][C:25]=1[OH:26])/[CH:5]=[CH:6]/[C:7]1[N:15]([CH3:16])[C:14]2[C:13](=[O:17])[N:12]([CH2:18][CH3:19])[C:11](=[O:20])[N:10]([CH2:21][CH3:22])[C:9]=2[N:8]=1.CI.[C:29](=O)([O-])[O-].[Li+].[Li+].O>CN(C)C=O.C(Cl)(Cl)Cl>[CH2:18]([N:12]1[C:13](=[O:17])[C:14]2[N:15]([CH3:16])[C:7](/[CH:6]=[CH:5]/[C:4]3[CH:23]=[CH:24][C:25]([O:26][CH3:29])=[C:2]([OH:1])[CH:3]=3)=[N:8][C:9]=2[N:10]([CH2:21][CH3:22])[C:11]1=[O:20])[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

Compound 173 (400 mg, 1.12 mmol) obtained in Reference Example 112 was dissolved in 8 ml of dimethylformamide. To the solution were added 0.35 ml (5.62 mmol) of methyl iodide and 415 mg (5.62 mmol) of lithium carbonate, and the mixture was stirred at 80° C. for 3.5 hours. Water was added thereto to dissolve lithium carbonate, followed by addition of chloroform. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate, followed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform) to give 127 mg (yield 76%) of Compound 174 as a pale brown powder. The obtained crude crystals were further recrystallized from ethanol.

Workup

washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous sodium sulfate
customfollowed by evaporation under reduced pressure
customThe residue was purified by silica gel column chromatography (eluent: chloroform)

Sources & evidence

ORD record: ord-432ab3bebf994982a3e85d8e42a9e9fa
Source dataset: uspto-grants-1996_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05484920

Reaction notes

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