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Trimethyl orthoformate → 7-tert-Butyl-3-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3H-quinazolin-4-one

HRID 68454
ノート
印刷プレビュー

反応式

HRID 68454 の反応式
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.[CH3:15][C:16]1[C:21]([B:22]2[O:26][C:25]([CH3:28])([CH3:27])[C:24]([CH3:30])([CH3:29])[O:23]2)=[CH:20][CH:19]=[CH:18][C:17]=1[NH2:31].[CH3:32]OC(OC)OC>C1(C)C=CC=CC=1>[C:11]([C:9]1[CH:10]=[C:2]2[C:3]([C:4](=[O:6])[N:31]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([B:22]4[O:26][C:25]([CH3:27])([CH3:28])[C:24]([CH3:30])([CH3:29])[O:23]4)[C:16]=3[CH3:15])[CH:32]=[N:1]2)=[CH:7][CH:8]=1)([CH3:14])([CH3:13])[CH3:12]
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 9005Trimethyl orthoformateHCID 146458722-Amino-4-tert-butylbenzoic acidHCID 467380052-Methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

生成物 1

HCID 580161917-tert-Butyl-3-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3H-quinazolin-4-one

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A solution of 2-Amino-4-tert-butyl-benzoic acid (78 mg, 0.41 mmol) in 2 mL trimethylorthoformate was heated to 105° C. for 30 minutes. The resulting solution was concentrated in vacuo. 2-Methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylamine (100 mg, 0.41 mmol) in 2 mL toluene was added. The resulting mixture was heated at reflux for 1 hour, concentrated in vacuo, and purified by flash chromatography (15% ethylacetate/hexanes) to yield 7-tert-Butyl-3-[2-methyl-3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-3H-quinazolin-4-one (68 mg, 0.16 mmol). MS (ESI) 419.2 (M+H)+.

後処理

  1. concentrationThe resulting solution was concentrated in vacuo
  2. temperatureThe resulting mixture was heated
  3. temperatureat reflux for 1 hour
  4. concentrationconcentrated in vacuo
  5. custompurified by flash chromatography (15% ethylacetate/hexanes)

出典と根拠

ORDレコード
ord-31175181f80a41b3b493d4b2dc90bcab
出典データセット
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08822457B2

反応ノート

読み込み中…

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