tert-Butyl methyl ether → (3-(5-Bromopyrimidin-2-yl)phenyl)methanol

HRID 330803ノート

反応式

HRID 330803 の反応式
[Br:1][C:2]1[CH:3]=[N:4][C:5](I)=[N:6][CH:7]=1.[OH:9][CH2:10][C:11]1[CH:12]=[C:13](B(O)O)[CH:14]=[CH:15][CH:16]=1.O.O.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].COC(C)(C)C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]([C:15]2[CH:16]=[C:11]([CH2:10][OH:9])[CH:12]=[CH:13][CH:14]=2)=[N:6][CH:7]=1

参加物

8

反応物 4

HCID 15413tert-Butyl methyl etherHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 70066515-Bromo-2-iodopyrimidineHCID 18407952Tripotassium phosphate trihydrate

生成物 1

HCID 59484879(3-(5-Bromopyrimidin-2-yl)phenyl)methanol

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒2 回HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

750 mg (0.65 mmol) of tetrakis(triphenylphosphine)palladium are added to a solution, kept under nitrogen, of 6.11 g (21.5 mmol) of 5-bromo-2-iodo-pyrimidine, 3.91 g (25.7 mmol) of 3-(hydroxymethyl)benzeneboronic acid and 9.11 g (42.9 mmol) of tripotassium phosphate trihydrate in 120 ml of dioxane and 14 ml of water, and the mixture is stirred at 90° C. for 18 hours. The reaction mixture is cooled to room temperature, tert-butyl methyl ether and water are added, and the mixture is filtered through kieselguhr. The organic phase of the filtrate is separated off, dried over sodium sulfate and evaporated. The residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent; product: 2.49 g;

後処理

  1. temperatureThe reaction mixture is cooled to room temperature
  2. filtrationthe mixture is filtered through kieselguhr
  3. customThe organic phase of the filtrate is separated off
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue is chromatographed on a silica-gel column with dichloromethane/methanol as eluent

出典と根拠

ORDレコード
ord-5f83a13a72554b6d8bc07ea54d0e89dc
出典データセット
uspto-grants-2014_11
特許番号
US08877751B2

反応ノート

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