Methanol → 6-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-pyrimidin-4(3H)-one

HRID 2059865

反応式

HRID 2059865 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[OH:9][C:10]([CH3:25])([CH3:24])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][C:14]=1[O:22][CH3:23].N1C=CC=CC=1.CO>C(Cl)Cl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]([C:16]2[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]([OH:9])([CH3:25])[CH3:24])=[C:14]([O:22][CH3:23])[CH:15]=2)[C:4](=[O:8])[CH:3]=1

参加物

6

反応物 4

HCID 887MethanolHCID 1049Pyridine2 回HCID 585798634-(2-Hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acidHCID 1354454786-Chloropyrimidin-4-ol

生成物 1

HCID 585799166-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-pyrimidin-4(3H)-one収率 46%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A mixture of 6-chloropyrimidin-4(3H)-one (50 mg, 0.383 mmol), 4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenylboronic acid Part D of Procedure 4 (184 mg, 0.766 mmol), copper (II) acetate, monohydrate (84 mg, 0.421 mmol), and pyridine (1.5 mL, 19.15 mmol) in DCM (4 mL) was stirred at RT under the presence of air overnight (21 hours). Pyridine (0.5 mL) and MeOH (0.5 mL) were added and continued to stir for 2 hours. The reaction was diluted with DCM, washed with 1N HCl, sat NaHCO3, dried (Na2SO4), and concentrated to afford crude product. The crude was purified using ISCO flash chromatography (silica gel/hexanes-ethyl acetate 100:0 to 0:100 gradient) to afford the desired product 6-chloro-3-(4-(2-hydroxy-2-methylpropoxy)-3-methoxyphenyl)-pyrimidin-4(3H)-one 11A (57.4 mg, 0.177 mmol, 46% yield) as a light brown solid.

後処理

  1. stirringto stir for 2 hours
  2. washwashed with 1N HCl
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customto afford crude product
  6. customThe crude was purified

出典と根拠

ORDレコード
ord-7602434f60244de98cdf58296eda172c
出典データセット
uspto-grants-2012_10
特許番号
US08278316B2

関連ノート

読み込み中…