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4-Nitrophenyl chloroformate → 6-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester

HRID 2362294
ノート
印刷プレビュー

反応式

HRID 2362294 の反応式
[CH3:1][O:2][C:3]([C:5]1[CH:6]([C:14]2[CH:19]=[CH:18][C:17]([C:20]#[N:21])=[CH:16][CH:15]=2)[N:7]=[C:8]([O:12][CH3:13])[NH:9][C:10]=1[CH3:11])=[O:4].Cl[C:23]([O:25][C:26]1[CH:31]=[CH:30][C:29]([N+:32]([O-:34])=[O:33])=[CH:28][CH:27]=1)=[O:24]>C(Cl)Cl.N1C=CC=CC=1>[N+:32]([C:29]1[CH:28]=[CH:27][C:26]([O:25][C:23]([N:7]2[CH:6]([C:14]3[CH:15]=[CH:16][C:17]([C:20]#[N:21])=[CH:18][CH:19]=3)[C:5]([C:3]([O:2][CH3:1])=[O:4])=[C:10]([CH3:11])[N:9]=[C:8]2[O:12][CH3:13])=[O:24])=[CH:31][CH:30]=1)([O-:34])=[O:33]
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

5

反応物 2

HCID 821294-Nitrophenyl chloroformateHCID 674375874-(4-Cyanophenyl)-2-methoxy-6-methyl-1,4-dihydropyrimidine-5-carboxylic acid methyl ester

生成物 1

HCID 866782176-(4-Cyanophenyl)-2-methoxy-4-methyl-6H-pyrimidine-1,5-dicarboxylic acid 5-methyl ester 1-(4-nitrophenyl) ester

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6344Dichloromethane
溶媒
2 回

反応条件

温度
0 °C

実験手順

Intermediate 4 (1.56 g, 5.46 mmol) was dissolved in a mixture of DCM (25 mL) and pyridine (10 mL) and cooled using an ice bath. A solution of 4-nitrophenyl chloroformate (705 mg, 3.50 mmol) in DCM (25 mL) was added over 30 minutes. The reaction mixture was stirred for 1 hour at 0° C. and then the solvent was removed in vacuo. The resulting residue was purified by silica gel chromatography eluting with a gradient of 0-20% EtOAc in cyclohexane to gave the title compound as a yellow solid. The product thus obtained was used in the subsequent step without further analysis (2.0 g).

後処理

  1. temperaturecooled
  2. customthe solvent was removed in vacuo
  3. customThe resulting residue was purified by silica gel chromatography
  4. washeluting with a gradient of 0-20% EtOAc in cyclohexane

出典と根拠

ORDレコード
ord-dc344d92d0684fb7bf23a36fdd584046
出典データセット
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08691826B2

反応ノート

読み込み中…

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