Water → HCID 23289167, compound

HRID 366332Notes

Reaction equation

[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]([NH:13][CH3:14])[CH3:12])[O:10][C:6]=2[C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:25])([F:24])[F:23])[N:17]([CH3:26])[C:16]2=[O:27])=[C:4]([F:28])[CH:3]=1.[C:29](=O)([O-])[O-].[K+].[K+].CI.O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[CH:8]=[C:9]([CH:11]([N:13]([CH3:29])[CH3:14])[CH3:12])[O:10][C:6]=2[C:5]([N:15]2[C:20](=[O:21])[CH:19]=[C:18]([C:22]([F:23])([F:25])[F:24])[N:17]([CH3:26])[C:16]2=[O:27])=[C:4]([F:28])[CH:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

0.5 g (1.2 mmol) of 3-[4-chloro-6-fluoro-2-(1-methylaminoethyl)benzofuran-7-yl]-1-methyl-6-trifluoromethyluracil and 0.40 g (2.9 mmol) of potassium carbonate were suspended in 50 ml of N,N-dimethylformamide, and 1.0 g (7.0 mmol) of methyl iodide was added thereto, followed by stirring at 60° C. for 2 hours. After completion of the reaction, the reaction solution was poured into water and extracted with ethyl acetate. The organic layer was washed sequentially with water and a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure. Then, the obtained residue was purified by silica gel column chromatography to obtain 0.35 g (yield: 68%) of the desired product as a purple glassy substance. Refractive index: 1.5341 (20° C.)

Workup

customAfter completion of the reaction
extractionextracted with ethyl acetate
washThe organic layer was washed sequentially with water
dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate
distillationThe solvent was distilled off under reduced pressure
customThen, the obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record: ord-b247628c007f4f8ea14b7c73d9ea5d91
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

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