Propargyl bromide → 1-Methyl-3-[1-(2-propynyl)-2-oxo-6-fluoro-1,2-dihydroquinoline-7-yl]-6-(trifluoromethyl)-pyrimidine-2,4(1H,3H)-dione
反応式
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[N:12]1[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]1=[O:24])[NH:8][C:7](=[O:25])[CH:6]=[CH:5]2.Br[CH2:27][C:28]#[CH:29].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:29]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([F:1])=[C:11]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=2)[CH:5]=[CH:6][C:7]1=[O:25])[C:28]#[CH:27]参加物
反応物 3
生成物 1
試薬・触媒・溶媒 1
実験手順
A stirred solution of 0.6 gram (0.002 mole) of 3-(6-fluoroquinolin-2-on-7-yl)-1-methyl-6-trifluoromethyluracil, 0.5 gram (0.003 mole) of 3-bromopropyne, and 0.5 gram (0.003 mole) of potassium carbonate in 40 mL of N,N-dimethylformamide was stirred at ambient temperature for about 16 hours. The reaction mixture was then subjected to column chromatography on silica gel. Elution was accomplished using 1:1 ethyl acetate-heptane and ethyl acetate. The product-containing fractions were combined and concentrated under reduced pressure, yielding 0.4 gram of 3-[1-(2-propyn-1-yl)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil, mp 236°-238° C. The NMR spectrum was consistent with the proposed structure. Other fractions were combined and concentrated under reduced pressure, yielding a small amount of the O-alkylated product, 3-[2-(2-propyn-1-yloxy)-6-fluoroquinolin-2-on-7-yl]-1-methyl-6-trifluoromethyluracil.
後処理
- washElution
- concentrationconcentrated under reduced pressure
出典と根拠
- ORDレコード
- ord-d4a377c007a041c5abf1cd88c5af2eaf
- 出典データセット
- uspto-grants-1994_05
- 特許番号
- US05310723
反応ノート
読み込み中…