Cesium fluoride → 3-(4-Chloro-2-ethylbenzofuran-7-yl)-1-methyl-6-trifluoromethyluracil

HRID 366313Notes

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]([O:21][CH:22]([CH3:25])[C:23]#[CH:24])[CH:3]=1.[F-].[Cs+]>C(N(CC)C1C=CC=CC=1)C>[Cl:1][C:2]1[C:3]2[CH:25]=[C:22]([CH2:23][CH3:24])[O:21][C:4]=2[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])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 185 °C

Procedure

50 ml of N,N-diethylaniline was added to 1.25 g (3.4 mmol) of 3-[4-chloro-2-(1-methyl-2-propynyloxy)phenyl]-1-methyl-6-trifluoromethyluracil and 1.0 g (6.8 mmol) of cesium fluoride, followed by stirring at 180 to 190° C. for 30 minutes. After completion of the reaction, the reaction mixture was purified directly by silica gel column chromatography to obtain 0.60 g (yield: 50.7%) of the desired product as white crystals. Melting point: 159-160° C.

Workup

customAfter completion of the reaction
customthe reaction mixture was purified directly by silica gel column chromatography

Sources & evidence

ORD record: ord-fa6db834ffd64fa6a6f83980b1c85715
Source dataset: uspto-grants-2000_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06130187

Reaction notes

Loading…