Piconol → 2-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine

HRID 1352739ノート

反応式

HRID 1352739 の反応式
[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([OH:22])=[O:21])=[CH:5][N:4]=1.ClC1C=C(Cl)C=C(Cl)C=1C(Cl)=O.CN(C1C=CC=CN=1)C.[N:44]1[CH:49]=[CH:48][CH:47]=[CH:46][C:45]=1[CH2:50]O>O1CCCC1.O.C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][S:2][C:3]1[N:8]=[C:7]([NH:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([Cl:19])[CH:12]=2)[C:6]([C:20]([O:22][CH2:50][C:45]2[CH:46]=[CH:47][CH:48]=[CH:49][N:44]=2)=[O:21])=[CH:5][N:4]=1

参加物

9

反応物 4

HCID 11474PiconolHCID 218852-DimethylaminopyridineHCID 27337032,4,6-Trichlorobenzoyl chlorideHCID 226655724-((3-Chloro-4-methoxybenzyl)amino)-2-(methylthio)pyrimidine-5-carboxylic acid

生成物 1

HCID 178483432-Methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine

試薬・触媒・溶媒 4

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A mixture of 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-carboxypyrimidine (prepared in Example 79) 0.100 g and triethylamine 82 μl in tetrahydrofuran 2.0 ml is treated under room temperature with 2,4,6-trichlorobenzoyl chloride 51 μl and then dimethylaminopyridine about 1 mg is added thereto, followed by stirring for 10 minutes. After addition of 2-pyridinemethanol 31 μl, the mixture is stirred for 12 hours. Ethyl acetate and water are added thereto and the organic layer is separated, washed with sodium hydrogen carbonate solution, brine. The organic layer is dried over anhydrous sodium sulfate and in vacuo. The residue is purified with silica gel chromatography (solvent; chloroform:ethyl acetate=5:1–2:1) and recrystallized from ethyl acetate-isopropyl ether to give 2-methylthio-4-(3-chloro-4-methoxybenzylamino)-5-(2-pyridylmethoxycarbonyl)pyrimidine as a colorless needle, 0.5183 g. mp117–118° C.

後処理

  1. stirringthe mixture is stirred for 12 hours
  2. customthe organic layer is separated
  3. washwashed with sodium hydrogen carbonate solution, brine
  4. dry with materialThe organic layer is dried over anhydrous sodium sulfate and in vacuo
  5. customThe residue is purified with silica gel chromatography (solvent; chloroform:ethyl acetate=5:1–2:1)
  6. customrecrystallized from ethyl acetate-isopropyl ether

出典と根拠

ORDレコード
ord-38caa3bcdfad4d71bf6ce9fd4799a052
出典データセット
uspto-grants-2007_05
特許番号
US07220736B2

反応ノート

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