Water → HCID 23289182, compound

HRID 366345Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:17])[F:16])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([OH:21])[CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]#[CH:30].O>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13](=[O:14])[CH:12]=[C:11]([C:15]([F:18])([F:16])[F:17])[N:10]([CH3:19])[C:9]2=[O:20])=[C:4]([O:21][CH2:30][C:29]#[CH:28])[CH:3]=1

Participants

Conditions

Temperature: 70 °C

Procedure

22.6 g (70.5 mmol) of 3-(4-chloro-2-hydroxyphenyl-1-methyl-6-trifluoromethyluracil and 14.5 g (105.1 mmol) of potassium carbonate were suspended in 150 ml of N,N-dimethylformamide, and 11.2 g (94.1 mmol) of propargyl bromide was dropwise added thereto at room temperature. After stirring at 70° C. for 2 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 22.5 g (yield: 89.0%) of the desired product as pale brown powder. Melting point: 147-148° 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-f72aa0496a88418b8cc777f287e1ee54
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

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