Butyl iodide → 6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid butyl ester

HRID 245304

反応式

HRID 245304 の反応式
[NH2:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=[C:4]([C:18]([OH:20])=[O:19])[C:3]=1[CH:21]=[CH2:22].I[CH2:24][CH2:25][CH2:26][CH3:27].C(=O)([O-])[O-].[Li+].[Li+]>CN(C=O)C>[CH2:24]([O:19][C:18]([C:4]1[C:3]([CH:21]=[CH2:22])=[C:2]([NH2:1])[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([O:15][CH3:16])[C:9]=2[F:17])[N:5]=1)=[O:20])[CH2:25][CH2:26][CH3:27]

参加物

5

反応物 3

HCID 10962Butyl iodideHCID 11125Lithium CarbonateHCID 468509124-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-ethenylpyrimidine-6-carboxylic acid

生成物 1

HCID 594320876-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid butyl ester収率 52.7%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

6-Amino-2-(4-chloro-2-fluoro-3-methoxyphenyl)-5-vinyl-pyrimidine-4-carboxylic acid (0.150 g, 0.46 mmol), iodobutane (0.111 g, 0.60 mmol), and lithium carbonate (0.044 g, 0.6 mmol) were combined in DMF (1.5 mL) and heated at 60° C. overnight. The cooled reaction mixture was concentrated and partitioned between ethyl acetate and water. The organic phase was dried and concentrated. The product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient) to yield the title compound (0.092 g, 52.3% yield): 1H NMR (CDCl3) δ 7.65 (dd, 1H), 7.19 (dd, 1H), 7.75 (dd, 1H), 5.62-5.67 (m, 2H), 5.35 (br s, 2H), 4.34 (t, 3H), 3.99 (dd, 3H), 1.74 (m, 2H), 1.45 (m, 2H), 0.97 (t, 3H).

後処理

  1. customThe cooled reaction mixture
  2. concentrationwas concentrated
  3. custompartitioned between ethyl acetate and water
  4. customThe organic phase was dried
  5. concentrationconcentrated
  6. customThe product was purified by flash chromatography on silica gel (ethyl acetate/hexane gradient)

出典と根拠

ORDレコード
ord-f1786629b665455cb6b49adf475e259f
出典データセット
uspto-grants-2014_02
特許番号
US08658791B2

関連ノート

読み込み中…