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Carbamimidic acid, methyl ester, sulfate (1:1) → 1,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester

HRID 1789577
ノート
印刷プレビュー

反応式

HRID 1789577 の反応式
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:17](=O)[CH3:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].S(O)(O)(=O)=O.[CH3:25][O:26][C:27](=[NH:29])[NH2:28].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH3:25][O:26][C:27]1[NH:29][C:17]([CH3:18])=[C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]([C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[N:28]=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 3

HCID 169039Carbamimidic acid, methyl ester, sulfate (1:1)HCID 367507Ethyl 2-(3-nitrobenzylidene)-3-oxobutanoateHCID 516892Sodium Bicarbonate

生成物 1

HCID 139125831,4-Dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester収率 75.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒
HCID 8857
Ethyl Acetate
溶媒

実験手順

A reaction mixture containing 2-[(3-nitrophenyl)methylene]-3-oxobutanoic acid, ethyl ester (2.62 g, 10.0 mmole), 2-methylpseudourea sulfate (1.72 g, 10.0 mmole), and sodium bicarbonate (2.52 g, 30.0 mmole) in dimethylformamide (10 ml) was heated at 65°-70° C. for 16 hours. The reaction mixture was allowed to cool to room temperature, diluted with ethyl acetate, and filtered. The filtrate was washed with water and brine, and then dried over anhydrous magnesium sulfate. Evaporation of the solvent gave a yellow oil which was purified by flash chromatography (5% ethyl acetate in dichloromethane). The resulting foam was crystallized from isopropyl ether/hexanes to provide 2.41 g of 1,4-dihydro-2-methoxy-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, ethyl ester as a colorless crystalline product; melting point 103.5°-105° C. TLC (silica gel; ethyl acetate: hexanes 50:50) Rf =0.31

後処理

  1. temperaturewas heated at 65°-70° C. for 16 hours
  2. filtrationfiltered
  3. washThe filtrate was washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customEvaporation of the solvent
  6. customgave a yellow oil which
  7. customwas purified by flash chromatography (5% ethyl acetate in dichloromethane)
  8. customThe resulting foam was crystallized from isopropyl ether/hexanes

出典と根拠

ORDレコード
ord-0a3b14c7b922485e955378c7884aefb2
出典データセット
uspto-grants-1987_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04689414

反応ノート

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