Water → HCID 23289169, compound

HRID 366347Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([OH:9])[C:3]=1[N:10]1[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[N:12]([CH3:21])[C:11]1=[O:22].C(=O)([O-])[O-].[K+].[K+].[CH2:29](Br)[C:30]#[CH:31].O>CN(C)C=O>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[C:4]([O:9][CH2:31][C:30]#[CH:29])[C:3]=1[N:10]1[C:15](=[O:16])[CH:14]=[C:13]([C:17]([F:20])([F:18])[F:19])[N:12]([CH3:21])[C:11]1=[O:22]

Participants

Conditions

Temperature: 65 °C

Procedure

4.8 g (15 mmol) of 3-(2,4-difluoro-6-hydroxyphenyl)-1-methyl-6-trifluoromethyluracil and 3.2 g (23 mmol) of potassium carbonate were suspended in 50 ml of N,N-dimethylformamide, and 2.5 g (21 mmol) of propargyl bromide was dropwise added thereto at room temperature. After stirring at from 60 to 70° C. for 5 hours, 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 crude crystals were washed with isopropyl ether to obtain 5.0 g (yield: 92.63%) of the desired product as yellowish brown powder. Melting point: 159-162° C.

Workup

customat room temperature
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 crude crystals
washwere washed with isopropyl ether

Sources & evidence

ORD record: ord-d81786abc69441d89d29f4f34ca3b94a
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

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