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Ethanol → 2-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

HRID 2267437
ノート
印刷プレビュー

反応式

HRID 2267437 の反応式
Br[C:2]1[S:6][C:5]([C:7]2[C:12]([C:13]#[N:14])=[CH:11][N:10]=[C:9]([NH:15][CH2:16][CH2:17][N:18]3[CH2:22][CH2:21][NH:20][C:19]3=[O:23])[N:8]=2)=[CH:4][CH:3]=1.[S:24]1[CH:28]=[CH:27][CH:26]=[C:25]1B(O)O.C(=O)([O-])[O-].[Na+].[Na+].C(O)C>ClCCl.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>[O:23]=[C:19]1[NH:20][CH2:21][CH2:22][N:18]1[CH2:17][CH2:16][NH:15][C:9]1[N:8]=[C:7]([C:5]2[S:6][C:2]([C:25]3[S:24][CH:28]=[CH:27][CH:26]=3)=[CH:3][CH:4]=2)[C:12]([C:13]#[N:14])=[CH:11][N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 27339602-Thiopheneboronic acidHCID 602045694-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile

生成物 1

HCID 602045672-(2-(2-Oxoimidazolidin-1-yl)ethylamino)-4-(5-(thiophen-2-yl)thiophen-2-yl)pyrimidine-5-carbonitrile

試薬・触媒・溶媒 2

HCID 178418397
HCID 178418397、化合物
触媒
HCID 6344Dichloromethane溶媒

反応条件

温度
130 °C

実験手順

4-(5-Bromothiophen-2-yl)-2-(2-(2-oxoimidazolidin-1-yl)ethylamino)pyrimidine-5-carbonitrile (0.08 g, 0.2 mmol), thiophen-2-ylboronic acid (0.052 g, 04 mmol), sodium carbonate (1.5 mL of 2 M solution, 1 mmol) were added to a microwave tube containing ethanol (1.5 mL). The tube was flushed with nitrogen and tetrakis(triphenylphosphine)palladium (0.06 g, 0.054 mmol) was added. The tube was capped and heated to 130° C. for 30 min in a Personal Chemistry microwave. The reaction was diluted with dichloromethane and washed with saturated aqueous sodium bicarbonate, water and brine. The organic layer was then dried with sodium sulfate, reduced in vacuo and purified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane to afford a yellow solid which recrystallized from ethyl acetate. Yield=0.066 g. MS (M+H)+ 397.

後処理

  1. additionwas added
  2. customThe tube was capped
  3. washwashed with saturated aqueous sodium bicarbonate, water and brine
  4. dry with materialThe organic layer was then dried with sodium sulfate
  5. custompurified by flash chromatography on silica gel using a gradient of 0 to 10% methanol in dichloromethane
  6. customto afford a yellow solid which
  7. customrecrystallized from ethyl acetate

出典と根拠

ORDレコード
ord-13821481fe2d4cca99d88871ec9c51f6
出典データセット
uspto-grants-2010_12
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07858785B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート