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

HRID 1722399
ノート
印刷プレビュー

反応式

HRID 1722399 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.[CH2:25]([N:27]([CH2:30]C)[CH2:28][CH3:29])C.C(Cl)(Cl)=[O:33].[CH:36]1C=[CH:40][CH:39]=[CH:38][CH:37]=1.C(CN)C1C=CC=CC=1>ClCCl>[CH3:30][N:27]([CH2:28][C:29]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[C:25]([N:8]1[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]=[C:3]1[O:2][CH3:1])=[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

7

反応物 5

HCID 241BenzeneHCID 1001PhenethylamineHCID 6371PhosgeneHCID 8471TriethylamineHCID 146271971,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methyethyl ester

生成物 1

HCID 14257071
1,6-Dihydro-1-[[methyl(phenylmethyl)amino]carbonyl]-2-methoxy-4-methyl-6-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, 1-methylethyl ester

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

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 (3.34 g, 10 mmol; see Example 2A) and dry triethylamine (6.3 ml, 45 mmol) in dichloromethane (10 ml) in an ice bath under argon was treated dropwise via syringe with 1.3M phosgene in benzene solution (9.2 ml, 12 mmol). The resulting mixture was stirred in the bath for 20 hours. After cooling to 0° C. with a fresh ice bath, the mixture was treated with benzylmethylamine (1.95 ml, 15 mmol) and stirred at room temperature overnight. The reaction was then diluted with dichloromethane and washed with water, saturated sodium chloride, dried (potassium carbonate) and evaporated. The residue was passed through a short pad of silica, eluting with 20% acetone/hexanes. The fractions were combined evaporated and triturated with isopropyl ether to give white crystals (4.11 g), melting point 145°-146° C. (softens 140° C.).

後処理

  1. stirringstirred at room temperature overnight
  2. washwashed with water, saturated sodium chloride
  3. dry with materialdried (potassium carbonate)
  4. customevaporated
  5. washeluting with 20% acetone/hexanes
  6. customThe fractions were combined evaporated
  7. customtriturated with isopropyl ether

出典と根拠

ORDレコード
ord-10e22d0b8d144bfc8cb77f4e8ab746d2
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

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