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Benzene → 1,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

HRID 1722401
ノート
印刷プレビュー

反応式

HRID 1722401 の反応式
[CH3:1][O:2][C:3]1[NH:4][C:5]([CH3:24])=[C:6]([C:18]([O:20][CH:21]([CH3:23])[CH3:22])=[O:19])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[N:8]=1.C(N(CC)CC)C.[C:32](Cl)(Cl)=[O:33].C1C=CC=CC=1.[CH2:42]([NH2:49])[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1.[Cl-].[Na+]>ClCCl.O>[CH3:1][O:2][C:3]1[N:8]([C:32]([NH:49][CH2:42][C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)=[O:33])[CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=2)[C:6]([C:18]([O:20][CH:21]([CH3:22])[CH3:23])=[O:19])=[C:5]([CH3:24])[N:4]=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

9

反応物 6

HCID 241BenzeneHCID 5234Sodium ChlorideHCID 6371PhosgeneHCID 7504BenzylamineHCID 8471TriethylamineHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

生成物 1

HCID 14855106
1,6-Dihydro-2-methoxy-4-methyl-6-(3-nitrophenyl)-1-[[(phenylmethyl)amino]carbonyl]-5-pyrimidinecarboxylic acid, 1-methylethyl ester

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A solution of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester (5.00 g, 15.0 mmol; see Example 2A) and dry triethylamine (6.27 ml, 45 mmol) in dichloromethane (45 ml) in an ice bath under argon was treated with a 1.2M solution of phosgene in benzene (15.0 ml, 18.0 mmol) via syringe. After stirring 4.0 hours at 0° C., the reaction was treated with benzyl amine (2.46 ml, 22.5 mmol) and stirred at ambient temperature overnight. The reaction was treated with water and saturated sodium chloride. The organic phase was evaporated and flash chromatographed (3% ethyl acetate in dichloromethane) to give the title compound as a yellow foam (6.20 g) TLC (5% ethyl acetate/dichlorolmethane) major spot, Rf =0.70.

後処理

  1. stirringstirred at ambient temperature overnight
  2. customThe organic phase was evaporated
  3. customflash chromatographed (3% ethyl acetate in dichloromethane)

出典と根拠

ORDレコード
ord-9ff8d6bdff9f46049dac2c5f377ec371
出典データセット
uspto-grants-1989_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04855301

反応ノート

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