ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Methyl acetoacetate → Methyl 2-(thien-2-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihyropyrimidin-5-carboxylate

HRID 425250
ノート
印刷プレビュー

反応式

HRID 425250 の反応式
Cl.[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([NH2:9])=[NH:8].[Cl:10][C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH:13]=O.[C:20]([O:26][CH3:27])(=[O:25])[CH2:21][C:22]([CH3:24])=O.C([O-])(=O)C.[Na+]>C(O)C>[S:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]1[NH:9][C:22]([CH3:24])=[C:21]([C:20]([O:26][CH3:27])=[O:25])[CH:13]([C:12]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][C:11]=2[Cl:10])[N:8]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 7757Methyl acetoacetateHCID 1450242-Chloro-4-fluorobenzaldehydeHCID 517045Sodium AcetateHCID 2781759Thiophene-2-carboximidamide Hydrochloride

生成物 1

HCID 25001238Methyl 2-(thien-2-yl)-4-(2-chloro-4-fluorophenyl)-6-methyl-1,4-dihyropyrimidin-5-carboxylate収率 30%

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

実験手順

2.164 mmol of 2-thienylformamidine hydrochloride (Schaefer F. C., Peters G. A., et al, J. Org. Chem.; 1961, 26(2): 412-418), 2.164 mmol of 2-chloro-4-fluorobenzaldehyde, 2.164 mmol of methyl acetoacetate and 2.2 mmol of sodium acetate in 10 ml of anhydrous ethanol was reacted under reflux for 20 hours and concentrated. Ethyl acetate and water were added to the reaction, and the phases were separated. The ethyl acetate layer was dried over anhydrous sodium sulfate and separated by a column chromatography to give 0.22 g of a yellow crystal (yield: 30%); 1H-NMR (400 MHz, CDCl3) δ 2.55 (3H, s, CH3); 3.62 (3H, s, CH3); 6.00 (1H, s, CH); 6.89-6.94 (1H, m, ArH); 7.03-7.05 (1H, dd, J1=4.80 Hz, J2=3.60 Hz, ArH); 7.11-7.14 (1H, m, ArH); 7.26-7.30 (1H, m, ArH); 7.33-7.34 (1H, d, J2=3.60 Hz, ArH); 7.44-7.45 (1H, d, J1=4.80 Hz ArH); MS (HREI) 344.0448 (M+).

後処理

  1. temperatureunder reflux for 20 hours
  2. concentrationconcentrated
  3. additionEthyl acetate and water were added to the reaction
  4. customthe phases were separated
  5. dry with materialThe ethyl acetate layer was dried over anhydrous sodium sulfate
  6. customseparated by a column chromatography

出典と根拠

ORDレコード
ord-5af85200ea7c4f7b9c883564a93cab19
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08106196B2

反応ノート

読み込み中…

このページの内容参加物実験手順後処理出典と根拠反応ノート